JPS61106577A - フロ−〔３，２−ｃ〕ピリジン誘導体、その製造法およびそれを含有する医薬組成物 - Google Patents
フロ−〔３，２−ｃ〕ピリジン誘導体、その製造法およびそれを含有する医薬組成物Info
- Publication number
- JPS61106577A JPS61106577A JP60214460A JP21446085A JPS61106577A JP S61106577 A JPS61106577 A JP S61106577A JP 60214460 A JP60214460 A JP 60214460A JP 21446085 A JP21446085 A JP 21446085A JP S61106577 A JPS61106577 A JP S61106577A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- hydrogen
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 title description 49
- WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical class N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- -1 ethylphenyl Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract description 3
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 3
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
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- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000013078 crystal Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
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- 239000001110 calcium chloride Substances 0.000 description 7
- 229910001628 calcium chloride Inorganic materials 0.000 description 7
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 230000005764 inhibitory process Effects 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- 235000019502 Orange oil Nutrition 0.000 description 4
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
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- 230000009870 specific binding Effects 0.000 description 3
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- YHXHHGDUANVQHE-UHFFFAOYSA-N 2-bromo-1-naphthalen-2-ylethanone Chemical compound C1=CC=CC2=CC(C(=O)CBr)=CC=C21 YHXHHGDUANVQHE-UHFFFAOYSA-N 0.000 description 2
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
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- 230000001988 toxicity Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Surface Acoustic Wave Elements And Circuit Networks Thereof (AREA)
- Mushroom Cultivation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8414842 | 1984-09-27 | ||
| FR8414842A FR2570701B1 (fr) | 1984-09-27 | 1984-09-27 | Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61106577A true JPS61106577A (ja) | 1986-05-24 |
Family
ID=9308136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60214460A Pending JPS61106577A (ja) | 1984-09-27 | 1985-09-26 | フロ−〔３，２−ｃ〕ピリジン誘導体、その製造法およびそれを含有する医薬組成物 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4661498A (enExample) |
| EP (1) | EP0178201B1 (enExample) |
| JP (1) | JPS61106577A (enExample) |
| KR (1) | KR860002508A (enExample) |
| AT (1) | ATE40554T1 (enExample) |
| AU (1) | AU573390B2 (enExample) |
| CA (1) | CA1291994C (enExample) |
| DE (1) | DE3568045D1 (enExample) |
| DK (1) | DK158953C (enExample) |
| ES (1) | ES8605522A1 (enExample) |
| FI (1) | FI82054C (enExample) |
| FR (1) | FR2570701B1 (enExample) |
| GR (1) | GR852356B (enExample) |
| HU (1) | HU192365B (enExample) |
| IL (1) | IL76535A0 (enExample) |
| NO (1) | NO162821C (enExample) |
| NZ (1) | NZ213620A (enExample) |
| PT (1) | PT81206B (enExample) |
| ZA (1) | ZA857457B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002526546A (ja) * | 1998-10-06 | 2002-08-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | α２アンタゴニストとしてのベンゾチエノ［３，２−ｃ］ピリジン類 |
| JP2002535334A (ja) * | 1999-01-19 | 2002-10-22 | ニューロサーチ、アクティーゼルスカブ | 縮合ヘテロ環状化合物及びこれを神経変性疾患の治療に使用する方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566775B1 (fr) * | 1984-06-27 | 1986-10-31 | Synthelabo | Derives de tetrahydro-4,5,6,7 furo ou 1h-pyrrolo(2,3-c)pyridine, leur preparation et leur application en therapeutique |
| FR2619112B1 (fr) * | 1987-08-07 | 1989-11-17 | Synthelabo | Derives de (piperidinyl-4)methyl-2 benzo(b)furo(2,3-c) pyridines, leur preparation et leur application en therapeutique |
| FR2635977B1 (fr) * | 1988-09-07 | 1992-05-15 | Synthelabo | Utilisation de derives de tetrahydro-4,5,6,7 furopyridines pour obtenir des medicaments destines au traitement de l'obesite |
| US5795784A (en) | 1996-09-19 | 1998-08-18 | Abbott Laboratories | Method of performing a process for determining an item of interest in a sample |
| US5856194A (en) | 1996-09-19 | 1999-01-05 | Abbott Laboratories | Method for determination of item of interest in a sample |
| UA52681C2 (uk) * | 1997-04-08 | 2003-01-15 | Янссен Фармацевтика Н.В. | Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі |
| JP4717216B2 (ja) | 1998-12-21 | 2011-07-06 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | α２−アンタゴニストとしてのベンズイソキサゾールおよびフェノン類 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (enExample) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
| DD210278A5 (de) * | 1982-03-05 | 1984-06-06 | Boehringer Ingelheim Kg | Verfahren zur herstellung neuer basisch substituierter 4-phenyl-4,5,6,7-tetrahydro-thieno-(2,3-c)pyridine |
-
1984
- 1984-09-27 FR FR8414842A patent/FR2570701B1/fr not_active Expired
-
1985
- 1985-09-06 DE DE8585401732T patent/DE3568045D1/de not_active Expired
- 1985-09-06 AT AT85401732T patent/ATE40554T1/de not_active IP Right Cessation
- 1985-09-06 EP EP85401732A patent/EP0178201B1/fr not_active Expired
- 1985-09-26 CA CA000491635A patent/CA1291994C/en not_active Expired - Fee Related
- 1985-09-26 GR GR852356A patent/GR852356B/el unknown
- 1985-09-26 DK DK435285A patent/DK158953C/da not_active IP Right Cessation
- 1985-09-26 JP JP60214460A patent/JPS61106577A/ja active Pending
- 1985-09-26 US US06/780,453 patent/US4661498A/en not_active Expired - Fee Related
- 1985-09-26 NZ NZ213620A patent/NZ213620A/en unknown
- 1985-09-26 PT PT81206A patent/PT81206B/pt not_active IP Right Cessation
- 1985-09-26 ES ES547315A patent/ES8605522A1/es not_active Expired
- 1985-09-26 FI FI853719A patent/FI82054C/fi not_active IP Right Cessation
- 1985-09-26 KR KR1019850007089A patent/KR860002508A/ko not_active Ceased
- 1985-09-26 ZA ZA857457A patent/ZA857457B/xx unknown
- 1985-09-26 NO NO853782A patent/NO162821C/no unknown
- 1985-09-26 HU HU853694A patent/HU192365B/hu not_active IP Right Cessation
- 1985-09-27 AU AU47952/85A patent/AU573390B2/en not_active Ceased
- 1985-09-29 IL IL76535A patent/IL76535A0/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002526546A (ja) * | 1998-10-06 | 2002-08-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | α２アンタゴニストとしてのベンゾチエノ［３，２−ｃ］ピリジン類 |
| JP2002535334A (ja) * | 1999-01-19 | 2002-10-22 | ニューロサーチ、アクティーゼルスカブ | 縮合ヘテロ環状化合物及びこれを神経変性疾患の治療に使用する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DK158953C (da) | 1991-01-14 |
| ES547315A0 (es) | 1986-03-16 |
| EP0178201A1 (fr) | 1986-04-16 |
| ES8605522A1 (es) | 1986-03-16 |
| US4661498A (en) | 1987-04-28 |
| PT81206B (pt) | 1988-01-22 |
| CA1291994C (en) | 1991-11-12 |
| AU573390B2 (en) | 1988-06-09 |
| FI853719L (fi) | 1986-03-28 |
| FI82054C (fi) | 1991-01-10 |
| ATE40554T1 (de) | 1989-02-15 |
| FI853719A0 (fi) | 1985-09-26 |
| AU4795285A (en) | 1986-04-10 |
| FR2570701A1 (fr) | 1986-03-28 |
| PT81206A (fr) | 1985-10-01 |
| FI82054B (fi) | 1990-09-28 |
| NO162821C (no) | 1990-02-21 |
| GR852356B (enExample) | 1986-01-28 |
| DK435285A (da) | 1986-03-28 |
| DK158953B (da) | 1990-08-06 |
| KR860002508A (ko) | 1986-04-26 |
| NZ213620A (en) | 1988-01-08 |
| DE3568045D1 (en) | 1989-03-09 |
| EP0178201B1 (fr) | 1989-02-01 |
| IL76535A0 (en) | 1986-02-28 |
| DK435285D0 (da) | 1985-09-26 |
| HU192365B (en) | 1987-05-28 |
| NO853782L (no) | 1986-04-01 |
| HUT38945A (en) | 1986-07-28 |
| NO162821B (no) | 1989-11-13 |
| FR2570701B1 (fr) | 1987-05-22 |
| ZA857457B (en) | 1986-05-28 |
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