CA2120301A1 - Thiadiazinones - Google Patents
ThiadiazinonesInfo
- Publication number
- CA2120301A1 CA2120301A1 CA002120301A CA2120301A CA2120301A1 CA 2120301 A1 CA2120301 A1 CA 2120301A1 CA 002120301 A CA002120301 A CA 002120301A CA 2120301 A CA2120301 A CA 2120301A CA 2120301 A1 CA2120301 A1 CA 2120301A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- dihydro
- ethyl
- thiadiazin
- compound
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 21
- -1 methylene-dioxy Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- FYXVFOSDEZAHNQ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[2-(dimethylamino)ethyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OC)C(OC)=C1 FYXVFOSDEZAHNQ-UHFFFAOYSA-N 0.000 claims 1
- IBMXVTWWSFPTGW-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[3-(dimethylamino)propyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCCN(C)C)N=C1C1=CC=C(OC)C(OC)=C1 IBMXVTWWSFPTGW-UHFFFAOYSA-N 0.000 claims 1
- KFJJKQPQLLMDIQ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[3-(dimethylamino)propyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(CCCN(C)C)C(=O)SC1 KFJJKQPQLLMDIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 description 3
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- CRVAECICDQAMRA-UHFFFAOYSA-N 6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)(F)F)C(OC)=C1 CRVAECICDQAMRA-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 241000556679 Pholis Species 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 238000004040 coloring Methods 0.000 description 2
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- 238000009472 formulation Methods 0.000 description 2
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- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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 |
|---|---|---|---|
| DE4310699A DE4310699A1 (de) | 1993-04-01 | 1993-04-01 | Thiadiazinone |
| DEP4310699.4 | 1993-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2120301A1 true CA2120301A1 (en) | 1994-10-02 |
Family
ID=6484473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002120301A Abandoned CA2120301A1 (en) | 1993-04-01 | 1994-03-30 | 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 |
Family Cites Families (5)
| 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 |
| US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
| ES2131506T3 (es) * | 1990-09-21 | 1999-08-01 | Rohm & Haas | Dihidropiridacinonas y piridacinonas como fungicidas. |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| SK38594A3 (en) | 1994-12-07 |
| AU5798394A (en) | 1994-10-06 |
| AU675488B2 (en) | 1997-02-06 |
| 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 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |