JP2002531556A5 - - Google Patents
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- JP2002531556A5 JP2002531556A5 JP2000586710A JP2000586710A JP2002531556A5 JP 2002531556 A5 JP2002531556 A5 JP 2002531556A5 JP 2000586710 A JP2000586710 A JP 2000586710A JP 2000586710 A JP2000586710 A JP 2000586710A JP 2002531556 A5 JP2002531556 A5 JP 2002531556A5
- Authority
- JP
- Japan
- Prior art keywords
- disorders
- formula
- chem
- disorder
- propylamine
- 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
- 238000000034 method Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 208000007848 Alcoholism Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 206010001584 alcohol abuse Diseases 0.000 description 4
- 208000025746 alcohol use disease Diseases 0.000 description 4
- 208000019906 panic disease Diseases 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 208000030990 Impulse-control disease Diseases 0.000 description 3
- 206010039966 Senile dementia Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 acrylic ester Chemical class 0.000 description 3
- 230000016571 aggressive behavior Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010041250 Social phobia Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 description 1
- XJGVVOAKITWCAB-UHFFFAOYSA-N 2-phenylmethoxyethanamine Chemical compound NCCOCC1=CC=CC=C1 XJGVVOAKITWCAB-UHFFFAOYSA-N 0.000 description 1
- JGYVHBXLANTDMO-UHFFFAOYSA-N 3-(2-methoxyphenoxy)propan-1-amine Chemical compound COC1=CC=CC=C1OCCCN JGYVHBXLANTDMO-UHFFFAOYSA-N 0.000 description 1
- BRVUZJVOHZQUSX-UHFFFAOYSA-N 3-(2-methoxyphenyl)propan-1-amine Chemical compound COC1=CC=CC=C1CCCN BRVUZJVOHZQUSX-UHFFFAOYSA-N 0.000 description 1
- KZLHWRUQUSVISJ-UHFFFAOYSA-N 3-(3-methoxyphenoxy)propan-1-amine Chemical compound COC1=CC=CC(OCCCN)=C1 KZLHWRUQUSVISJ-UHFFFAOYSA-N 0.000 description 1
- CMIXSQAFEPGHMA-UHFFFAOYSA-N 3-(3-methoxyphenyl)propan-1-amine Chemical compound COC1=CC=CC(CCCN)=C1 CMIXSQAFEPGHMA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010041247 Social fear Diseases 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 description 1
- 229960000647 gepirone Drugs 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229950003599 ipsapirone Drugs 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11136098P | 1998-12-08 | 1998-12-08 | |
| DKPA199801631 | 1998-12-09 | ||
| DK60/111,360 | 1998-12-09 | ||
| DK199801631 | 1998-12-09 | ||
| PCT/DK1999/000676 WO2000034263A1 (en) | 1998-12-08 | 1999-12-03 | Benzofuran derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002531556A JP2002531556A (ja) | 2002-09-24 |
| JP2002531556A5 true JP2002531556A5 (https=) | 2006-12-14 |
Family
ID=43768792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000586710A Pending JP2002531556A (ja) | 1998-12-08 | 1999-12-03 | ベンゾフラン誘導体、その製造方法及びその使用方法 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1137644B9 (https=) |
| JP (1) | JP2002531556A (https=) |
| AR (1) | AR021509A1 (https=) |
| AT (1) | ATE249451T1 (https=) |
| AU (1) | AU759248B2 (https=) |
| CA (1) | CA2353618A1 (https=) |
| CZ (1) | CZ20012041A3 (https=) |
| DE (1) | DE69911243T2 (https=) |
| DK (1) | DK1137644T3 (https=) |
| ES (1) | ES2204175T3 (https=) |
| HU (1) | HUP0104510A3 (https=) |
| IL (1) | IL143082A (https=) |
| ME (1) | MEP38508A (https=) |
| PT (1) | PT1137644E (https=) |
| RS (1) | RS50065B (https=) |
| SE (1) | SE1137644T5 (https=) |
| SI (1) | SI1137644T1 (https=) |
| WO (1) | WO2000034263A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| EA008372B1 (ru) * | 2000-07-07 | 2007-04-27 | Х.Лундбекк А/С | Применение эсциталопрама для лечения расстройства, связанного с социальной тревогой |
| EA008373B1 (ru) * | 2000-07-07 | 2007-04-27 | Х. Лундбекк А/С | Применение эсциталопрама для лечения расстройства, связанного с посттравматическим стрессом |
| WO2002008216A1 (en) | 2000-07-21 | 2002-01-31 | H. Lundbeck A/S | Novel compounds and their use as glycine transport inhibitors |
| WO2002020493A2 (en) * | 2000-09-06 | 2002-03-14 | Chugai Seiyaku Kabushiki Kaisha | A traceless solid-phase synthesis of 2-imidazolones |
| US7276603B2 (en) | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
| US7235569B2 (en) | 2003-05-02 | 2007-06-26 | Wyeth | Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| EP4347559A4 (en) * | 2021-06-02 | 2025-04-09 | Saint Joseph's University | FLUORINATED TRYPTAMINE COMPOUNDS, RELATED ANALOGUES AND METHODS USING THEM |
| WO2025104490A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (https=) * | 1965-03-18 | |||
| GB1173312A (en) * | 1966-03-17 | 1969-12-10 | Kefalas As | Heterocyclic Compounds |
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| CA2176722A1 (en) * | 1993-12-28 | 1995-07-06 | Ruth E. Ten Brink | Heterocyclic compounds for the treatment of cns and cardiovascular disorders |
| ZA954689B (en) * | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
-
1999
- 1999-12-01 AR ARP990106110A patent/AR021509A1/es unknown
- 1999-12-03 PT PT99957263T patent/PT1137644E/pt unknown
- 1999-12-03 IL IL14308299A patent/IL143082A/en not_active IP Right Cessation
- 1999-12-03 HU HU0104510A patent/HUP0104510A3/hu unknown
- 1999-12-03 WO PCT/DK1999/000676 patent/WO2000034263A1/en not_active Ceased
- 1999-12-03 CZ CZ20012041A patent/CZ20012041A3/cs unknown
- 1999-12-03 DK DK99957263T patent/DK1137644T3/da active
- 1999-12-03 ES ES99957263T patent/ES2204175T3/es not_active Expired - Lifetime
- 1999-12-03 EP EP99957263A patent/EP1137644B9/en not_active Expired - Lifetime
- 1999-12-03 AU AU15036/00A patent/AU759248B2/en not_active Ceased
- 1999-12-03 JP JP2000586710A patent/JP2002531556A/ja active Pending
- 1999-12-03 SE SE99957263T patent/SE1137644T5/xx unknown
- 1999-12-03 CA CA002353618A patent/CA2353618A1/en not_active Abandoned
- 1999-12-03 RS YUP-384/01A patent/RS50065B/sr unknown
- 1999-12-03 AT AT99957263T patent/ATE249451T1/de not_active IP Right Cessation
- 1999-12-03 SI SI9930412T patent/SI1137644T1/xx unknown
- 1999-12-03 ME MEP-385/08A patent/MEP38508A/xx unknown
- 1999-12-03 DE DE69911243T patent/DE69911243T2/de not_active Expired - Fee Related
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