AU2001257230B2 - Ultrashort acting hypnotic barbiturates - Google Patents
Ultrashort acting hypnotic barbiturates Download PDFInfo
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- AU2001257230B2 AU2001257230B2 AU2001257230A AU2001257230A AU2001257230B2 AU 2001257230 B2 AU2001257230 B2 AU 2001257230B2 AU 2001257230 A AU2001257230 A AU 2001257230A AU 2001257230 A AU2001257230 A AU 2001257230A AU 2001257230 B2 AU2001257230 B2 AU 2001257230B2
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- Prior art keywords
- alkyl
- unbranched
- branched
- unsaturated
- hydrogen
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- 229940125717 barbiturate Drugs 0.000 title description 34
- 230000000147 hypnotic effect Effects 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 90
- 229920006395 saturated elastomer Polymers 0.000 claims description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 59
- -1 menthyl Chemical group 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000001961 anticonvulsive agent Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 230000001773 anti-convulsant effect Effects 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- XRMDCWJNPDVAFI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[N+]1=O XRMDCWJNPDVAFI-UHFFFAOYSA-N 0.000 claims 1
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- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/66—Thiobarbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19914400P | 2000-04-24 | 2000-04-24 | |
| US60/199,144 | 2000-04-24 | ||
| PCT/US2001/013246 WO2001081319A2 (en) | 2000-04-24 | 2001-04-24 | Ultrashort acting hypnotic barbiturates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001257230A1 AU2001257230A1 (en) | 2002-01-24 |
| AU2001257230B2 true AU2001257230B2 (en) | 2006-09-14 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001257230A Ceased AU2001257230B2 (en) | 2000-04-24 | 2001-04-24 | Ultrashort acting hypnotic barbiturates |
| AU5723001A Pending AU5723001A (en) | 2000-04-24 | 2001-04-24 | Ultrashort acting hypnotic barbiturates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU5723001A Pending AU5723001A (en) | 2000-04-24 | 2001-04-24 | Ultrashort acting hypnotic barbiturates |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6387914B2 (https=) |
| EP (1) | EP1276728A2 (https=) |
| JP (1) | JP2003531196A (https=) |
| AU (2) | AU2001257230B2 (https=) |
| CA (1) | CA2404898A1 (https=) |
| WO (1) | WO2001081319A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001257230B2 (en) | 2000-04-24 | 2006-09-14 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
| US6750238B1 (en) | 2000-05-12 | 2004-06-15 | The University Of Toledo | Aralkyl ester soft drugs |
| US6756047B2 (en) * | 2000-05-12 | 2004-06-29 | The University Of Toledo | Method and compositions for treating persistent pulmonary hypertension using aralkyl ester soft drugs |
| US7049326B2 (en) * | 2000-05-12 | 2006-05-23 | The University Of Toledo | Method and compositions for temporarily incapacitating subjects |
| US10537061B2 (en) * | 2010-02-26 | 2020-01-21 | Cnh Industrial America Llc | System and method for controlling harvest operations |
| WO2014014960A1 (en) * | 2012-07-16 | 2014-01-23 | Dignity Health | Treating of epilepsy and alcohol addiction with creatine |
| CA2961410C (en) | 2014-09-16 | 2023-07-11 | India Globalization Capital, Inc. | Cannabinoid composition and method for treating pain |
| CA2974895A1 (en) | 2015-01-25 | 2016-07-28 | India Globalization Capital, Inc. | Composition and method for treating seizure disorders |
| US10596159B2 (en) | 2015-08-12 | 2020-03-24 | India Globalization Capital, Inc. | Method and composition for treating cachexia and eating disorders |
| EP3471746A4 (en) | 2016-06-15 | 2020-02-26 | India Globalization Capital, Inc. | METHOD AND COMPOSITION FOR TREATING CRAMPING SEASONS |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2405732A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Ekto- und endoparasitenmittel |
| US4237270A (en) * | 1975-02-17 | 1980-12-02 | Spofa, United Pharmaceutical Works | Derivatives of carboxyalkyl imino- and thioxo-barbituric acids |
| US4634707A (en) * | 1983-12-19 | 1987-01-06 | Uniroyal Chemical Company | 5-Pyrimidinecarboxamides and treatment of leukemia and tumors therewith |
| WO1991008191A1 (en) * | 1989-11-14 | 1991-06-13 | Sloan-Kettering Institute For Cancer Research | Novel potent inducers of terminal differentiation and method of use thereof |
| WO1993020064A1 (en) * | 1992-04-06 | 1993-10-14 | Biosite Diagnostics Incorporated | Novel barbiturate derivatives and protein and polypeptide barbiturate derivative conjugates and labels |
| WO1998058925A1 (en) * | 1997-06-21 | 1998-12-30 | Roche Diagnostics Gmbh | Barbituric acid derivatives with antimetastatic and antitumor activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH678394A5 (https=) * | 1990-08-22 | 1991-09-13 | Cerny Erich H | |
| JPH06214344A (ja) * | 1992-10-22 | 1994-08-05 | Konica Corp | ハロゲン化銀写真感光材料 |
| JPH07120865A (ja) * | 1993-10-21 | 1995-05-12 | Konica Corp | ハロゲン化銀写真感光材料 |
| AU2001257230B2 (en) | 2000-04-24 | 2006-09-14 | Aryx Therapeutics | Ultrashort acting hypnotic barbiturates |
-
2001
- 2001-04-24 AU AU2001257230A patent/AU2001257230B2/en not_active Ceased
- 2001-04-24 JP JP2001578413A patent/JP2003531196A/ja active Pending
- 2001-04-24 US US09/841,738 patent/US6387914B2/en not_active Expired - Fee Related
- 2001-04-24 EP EP01930722A patent/EP1276728A2/en not_active Withdrawn
- 2001-04-24 AU AU5723001A patent/AU5723001A/xx active Pending
- 2001-04-24 CA CA002404898A patent/CA2404898A1/en not_active Abandoned
- 2001-04-24 WO PCT/US2001/013246 patent/WO2001081319A2/en not_active Ceased
-
2002
- 2002-05-13 US US10/145,601 patent/US6683086B2/en not_active Expired - Fee Related
-
2004
- 2004-01-23 US US10/763,904 patent/US7041673B2/en not_active Ceased
-
2007
- 2007-12-20 US US12/009,446 patent/USRE41289E1/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2405732A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Ekto- und endoparasitenmittel |
| US4237270A (en) * | 1975-02-17 | 1980-12-02 | Spofa, United Pharmaceutical Works | Derivatives of carboxyalkyl imino- and thioxo-barbituric acids |
| US4634707A (en) * | 1983-12-19 | 1987-01-06 | Uniroyal Chemical Company | 5-Pyrimidinecarboxamides and treatment of leukemia and tumors therewith |
| WO1991008191A1 (en) * | 1989-11-14 | 1991-06-13 | Sloan-Kettering Institute For Cancer Research | Novel potent inducers of terminal differentiation and method of use thereof |
| WO1993020064A1 (en) * | 1992-04-06 | 1993-10-14 | Biosite Diagnostics Incorporated | Novel barbiturate derivatives and protein and polypeptide barbiturate derivative conjugates and labels |
| WO1998058925A1 (en) * | 1997-06-21 | 1998-12-30 | Roche Diagnostics Gmbh | Barbituric acid derivatives with antimetastatic and antitumor activity |
Non-Patent Citations (2)
| Title |
|---|
| Chemical Abstract AN: 126:225269 * |
| Mirek J. et al,. Pol. J. Pharmacol., 1978, 30, 6850693 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2404898A1 (en) | 2001-11-01 |
| USRE41289E1 (en) | 2010-04-27 |
| US20030100575A1 (en) | 2003-05-29 |
| EP1276728A2 (en) | 2003-01-22 |
| WO2001081319A2 (en) | 2001-11-01 |
| AU5723001A (en) | 2001-11-07 |
| WO2001081319A3 (en) | 2002-05-16 |
| US6683086B2 (en) | 2004-01-27 |
| US6387914B2 (en) | 2002-05-14 |
| US7041673B2 (en) | 2006-05-09 |
| US20040167143A1 (en) | 2004-08-26 |
| US20020013330A1 (en) | 2002-01-31 |
| JP2003531196A (ja) | 2003-10-21 |
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