CS114291A3 - Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them - Google Patents
Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them Download PDFInfo
- Publication number
- CS114291A3 CS114291A3 CS911142A CS114291A CS114291A3 CS 114291 A3 CS114291 A3 CS 114291A3 CS 911142 A CS911142 A CS 911142A CS 114291 A CS114291 A CS 114291A CS 114291 A3 CS114291 A3 CS 114291A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- dione
- general formula
- benzothieno
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 5
- 241000551547 Dione <red algae> Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 239000001119 stannous chloride Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
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- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 abstract description 7
- JZFCFMFLPKVLRY-UHFFFAOYSA-N 1,4-dihydro-[1]benzothiolo[2,3-b]pyrazine-2,3-dione Chemical class S1C2=CC=CC=C2C2=C1NC(=O)C(=O)N2 JZFCFMFLPKVLRY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
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- -1 glycine-activated chloride Chemical class 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HCKUBNLZMKAEIN-UHFFFAOYSA-N 3-amino-1-hydroxypyrrolidin-2-one Chemical compound NC1CCN(O)C1=O HCKUBNLZMKAEIN-UHFFFAOYSA-N 0.000 description 3
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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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK101290A DK101290D0 (da) | 1990-04-24 | 1990-04-24 | Heterocykliske forbindelser, deres fremstilling og anvendelse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS114291A3 true CS114291A3 (en) | 1992-01-15 |
Family
ID=8100008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS911142A CS114291A3 (en) | 1990-04-24 | 1991-04-22 | Benzothieno-[2,3-b] pyrazine-2,3-(1h,4h) diones, processes for their preparation and a pharmaceutical comprising them |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5182279A (fi) |
| EP (1) | EP0526588B1 (fi) |
| JP (1) | JPH05507468A (fi) |
| AT (1) | ATE102626T1 (fi) |
| AU (1) | AU640230B2 (fi) |
| CA (1) | CA2081201A1 (fi) |
| CS (1) | CS114291A3 (fi) |
| DE (1) | DE69101378T2 (fi) |
| DK (2) | DK101290D0 (fi) |
| ES (1) | ES2062819T3 (fi) |
| FI (1) | FI99014C (fi) |
| HU (1) | HUT67021A (fi) |
| IE (1) | IE73246B1 (fi) |
| IL (1) | IL97913A (fi) |
| NO (1) | NO300776B1 (fi) |
| NZ (1) | NZ237921A (fi) |
| PT (1) | PT97479B (fi) |
| WO (1) | WO1991016325A1 (fi) |
| ZA (1) | ZA913084B (fi) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07505908A (ja) * | 1992-09-28 | 1995-06-29 | マックセチーニ、マリア ルイザ | Ｎｍｄａ受容体のアロステリックモジュレーター |
| FR2696466B1 (fr) * | 1992-10-02 | 1994-11-25 | Rhone Poulenc Rorer Sa | Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant. |
| AU680632B2 (en) | 1992-10-13 | 1997-08-07 | Neurosearch A/S | Quinoxalinedione derivatives as EAA antagonists |
| DK12293D0 (da) * | 1993-02-02 | 1993-02-02 | Novo Nordisk As | Heterocykliske forbindelser og deres fremstilling og anvendelse |
| FR2707645B1 (fr) * | 1993-07-16 | 1995-08-11 | Rhone Poulenc Rorer Sa | Dérivés d'imidazo[1,2-a]pirazine-4-one, leur préparation et les médicaments les contenant. |
| FR2726275B1 (fr) * | 1994-11-02 | 1996-12-06 | Rhone Poulenc Rorer Sa | Spiro heterocycle-imidazo(1,2-a)indeno(1,2-e)pyrazine)-4'- ones, leur preparation et les medicaments les contenants |
| WO1999046267A1 (en) * | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| US6262044B1 (en) | 1998-03-12 | 2001-07-17 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPASES) |
| MA38461B1 (fr) * | 2013-03-14 | 2021-10-29 | Curadev Pharma Private Ltd | Inhibiteurs de la voie de la kynurénine |
| WO2018122664A1 (en) * | 2016-12-28 | 2018-07-05 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, organic compound, light-emitting device, electronic device, and lighting device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA903588B (en) * | 1989-05-16 | 1991-02-27 | Merrell Dow Pharma | Excitatory amino acid antagonists |
-
1990
- 1990-04-24 DK DK101290A patent/DK101290D0/da not_active Application Discontinuation
-
1991
- 1991-04-18 US US07/688,008 patent/US5182279A/en not_active Expired - Fee Related
- 1991-04-22 IE IE132991A patent/IE73246B1/en not_active IP Right Cessation
- 1991-04-22 CS CS911142A patent/CS114291A3/cs unknown
- 1991-04-22 IL IL9791391A patent/IL97913A/en not_active IP Right Cessation
- 1991-04-23 WO PCT/DK1991/000105 patent/WO1991016325A1/en active IP Right Grant
- 1991-04-23 EP EP91919028A patent/EP0526588B1/en not_active Expired - Lifetime
- 1991-04-23 DK DK91919028.0T patent/DK0526588T3/da active
- 1991-04-23 CA CA002081201A patent/CA2081201A1/en not_active Abandoned
- 1991-04-23 JP JP91508446A patent/JPH05507468A/ja active Pending
- 1991-04-23 NZ NZ237921A patent/NZ237921A/en unknown
- 1991-04-23 ES ES91919028T patent/ES2062819T3/es not_active Expired - Lifetime
- 1991-04-23 AU AU77736/91A patent/AU640230B2/en not_active Ceased
- 1991-04-23 AT AT91919028T patent/ATE102626T1/de not_active IP Right Cessation
- 1991-04-23 HU HU9203325A patent/HUT67021A/hu unknown
- 1991-04-23 DE DE69101378T patent/DE69101378T2/de not_active Expired - Fee Related
- 1991-04-24 ZA ZA913084A patent/ZA913084B/xx unknown
- 1991-04-24 PT PT97479A patent/PT97479B/pt not_active IP Right Cessation
-
1992
- 1992-10-23 FI FI924829A patent/FI99014C/fi not_active IP Right Cessation
- 1992-10-23 NO NO924120A patent/NO300776B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO924120L (no) | 1992-10-23 |
| DE69101378D1 (de) | 1994-04-14 |
| ATE102626T1 (de) | 1994-03-15 |
| WO1991016325A1 (en) | 1991-10-31 |
| FI99014C (fi) | 1997-09-25 |
| US5182279A (en) | 1993-01-26 |
| CA2081201A1 (en) | 1991-10-25 |
| FI924829A0 (fi) | 1992-10-23 |
| AU7773691A (en) | 1991-11-11 |
| HUT67021A (en) | 1995-01-30 |
| ZA913084B (en) | 1992-02-26 |
| EP0526588A1 (en) | 1993-02-10 |
| HU9203325D0 (en) | 1993-01-28 |
| EP0526588B1 (en) | 1994-03-09 |
| IE73246B1 (en) | 1997-05-21 |
| IL97913A0 (en) | 1992-06-21 |
| IL97913A (en) | 1995-01-24 |
| ES2062819T3 (es) | 1994-12-16 |
| NO300776B1 (no) | 1997-07-21 |
| DK0526588T3 (da) | 1994-08-22 |
| FI99014B (fi) | 1997-06-13 |
| DK101290D0 (da) | 1990-04-24 |
| IE911329A1 (en) | 1991-11-06 |
| NO924120D0 (no) | 1992-10-23 |
| JPH05507468A (ja) | 1993-10-28 |
| FI924829A (fi) | 1992-10-23 |
| NZ237921A (en) | 1993-08-26 |
| DE69101378T2 (de) | 1994-06-16 |
| AU640230B2 (en) | 1993-08-19 |
| PT97479A (pt) | 1992-01-31 |
| PT97479B (pt) | 1998-08-31 |
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