AU675488B2 - Thiadiazinones - Google Patents
Thiadiazinones Download PDFInfo
- Publication number
- AU675488B2 AU675488B2 AU57983/94A AU5798394A AU675488B2 AU 675488 B2 AU675488 B2 AU 675488B2 AU 57983/94 A AU57983/94 A AU 57983/94A AU 5798394 A AU5798394 A AU 5798394A AU 675488 B2 AU675488 B2 AU 675488B2
- Authority
- AU
- Australia
- Prior art keywords
- dihydro
- ethyl
- thiadiazin
- methoxy
- formula
- 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.)
- Expired - Fee Related
Links
- -1 methylene- dioxy Chemical group 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- WIVMBQZZIYHVCZ-UHFFFAOYSA-N 6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1 WIVMBQZZIYHVCZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- 238000009472 formulation Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- LPVPITJSBXSDHT-UHFFFAOYSA-N 3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound O=C1NN=CCS1 LPVPITJSBXSDHT-UHFFFAOYSA-N 0.000 claims description 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- LVKFSJWCSIBHMY-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=NNC(=O)SC1CC LVKFSJWCSIBHMY-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- CYVXGBWDJPWDNC-UHFFFAOYSA-N 3-(3-ethoxy-4-methoxyphenyl)-6-ethyl-6H-1,3,4-thiadiazin-2-one Chemical compound C(C)OC=1C=C(C=CC=1OC)N1C(SC(C=N1)CC)=O CYVXGBWDJPWDNC-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
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- KYTOLIPSUUEDHP-UHFFFAOYSA-N 5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OC(F)F)=C1 KYTOLIPSUUEDHP-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4310699 | 1993-04-01 | ||
| DE4310699A DE4310699A1 (de) | 1993-04-01 | 1993-04-01 | Thiadiazinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5798394A AU5798394A (en) | 1994-10-06 |
| AU675488B2 true AU675488B2 (en) | 1997-02-06 |
Family
ID=6484473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU57983/94A Expired - Fee Related AU675488B2 (en) | 1993-04-01 | 1994-03-23 | Thiadiazinones |
Country Status (12)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500558A1 (de) * | 1995-01-11 | 1996-07-18 | Merck Patent Gmbh | 3-Alkoxycarbonyl-thiadiazinone |
| DE19502699A1 (de) * | 1995-01-28 | 1996-08-01 | Merck Patent Gmbh | Arylalkyl-thiadiazinone |
| DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| DK1355669T3 (da) * | 2000-08-10 | 2011-11-21 | Cold Spring Harbor Lab | Forbedret kognitiv træning |
| US8153646B2 (en) * | 2000-08-10 | 2012-04-10 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| EP1368035A1 (en) * | 2001-02-12 | 2003-12-10 | MERCK PATENT GmbH | Use of type 4 phosphodiesterase inhibitors in myocardial diseases |
| DE10150517A1 (de) * | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
| CN1578665A (zh) * | 2001-10-31 | 2005-02-09 | 默克专利股份公司 | 4型磷酸二脂酶抑制剂及其应用 |
| US20080227790A1 (en) * | 2004-02-04 | 2008-09-18 | Altana Pharma Ag | Pyridazinone Derivatives and their Use as Pde4 Inhibitors |
| JP4778449B2 (ja) | 2004-02-04 | 2011-09-21 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅ４インヒビターとしての２−（ピペリジン−４−イル）−４，５−ジヒドロ−２ｈ−ピリダジン−３−オン誘導体 |
| DE102007041115A1 (de) * | 2007-08-30 | 2009-03-05 | Merck Patent Gmbh | Thiadiazinonderivate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
| AU8460291A (en) * | 1990-09-21 | 1992-03-26 | Dow Agrosciences Llc | Dihydrohyridazinones, pyridazinones and related compounds as fungicides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4413713Y1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-04-26 | 1969-06-09 | ||
| JPS54135785A (en) * | 1978-04-12 | 1979-10-22 | Yoshitomi Pharmaceut Ind Ltd | Pyridazinone derivative and its preparation |
| US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
-
1993
- 1993-04-01 DE DE4310699A patent/DE4310699A1/de not_active Withdrawn
-
1994
- 1994-03-19 EP EP94104349A patent/EP0618201A1/de not_active Withdrawn
- 1994-03-23 AU AU57983/94A patent/AU675488B2/en not_active Expired - Fee Related
- 1994-03-25 CZ CZ94705A patent/CZ70594A3/cs unknown
- 1994-03-28 JP JP6057099A patent/JPH072812A/ja active Pending
- 1994-03-29 NO NO941150A patent/NO941150L/no unknown
- 1994-03-30 CA CA002120301A patent/CA2120301A1/en not_active Abandoned
- 1994-03-30 TW TW083102744A patent/TW310326B/zh active
- 1994-03-30 CN CN94104074A patent/CN1101644A/zh active Pending
- 1994-03-31 HU HU9400934A patent/HUT70543A/hu unknown
- 1994-03-31 US US08/220,657 patent/US5434149A/en not_active Expired - Fee Related
- 1994-03-31 SK SK385-94A patent/SK38594A3/sk unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
| AU8460291A (en) * | 1990-09-21 | 1992-03-26 | Dow Agrosciences Llc | Dihydrohyridazinones, pyridazinones and related compounds as fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| SK38594A3 (en) | 1994-12-07 |
| AU5798394A (en) | 1994-10-06 |
| NO941150D0 (no) | 1994-03-29 |
| US5434149A (en) | 1995-07-18 |
| EP0618201A1 (de) | 1994-10-05 |
| CN1101644A (zh) | 1995-04-19 |
| CZ70594A3 (en) | 1994-12-15 |
| CA2120301A1 (en) | 1994-10-02 |
| HU9400934D0 (en) | 1994-06-28 |
| TW310326B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-07-11 |
| DE4310699A1 (de) | 1994-10-06 |
| NO941150L (no) | 1994-10-03 |
| HUT70543A (en) | 1995-10-30 |
| JPH072812A (ja) | 1995-01-06 |
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