CA2404898A1 - Ultrashort acting hypnotic barbiturates - Google Patents
Ultrashort acting hypnotic barbiturates Download PDFInfo
- Publication number
- CA2404898A1 CA2404898A1 CA002404898A CA2404898A CA2404898A1 CA 2404898 A1 CA2404898 A1 CA 2404898A1 CA 002404898 A CA002404898 A CA 002404898A CA 2404898 A CA2404898 A CA 2404898A CA 2404898 A1 CA2404898 A1 CA 2404898A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydrogen
- branched
- unbranched
- saturated
- 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
- 229940125717 barbiturate Drugs 0.000 title abstract description 35
- 230000000147 hypnotic effect Effects 0.000 title abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229920006395 saturated elastomer Polymers 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 51
- -1 menthyl Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000001961 anticonvulsive agent Substances 0.000 claims description 10
- 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 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000004799 sedative–hypnotic effect Effects 0.000 claims description 7
- 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 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 5
- 230000001773 anti-convulsant effect Effects 0.000 claims description 5
- 125000005425 toluyl group Chemical group 0.000 claims description 5
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 239000002253 acid Substances 0.000 abstract description 14
- 239000002207 metabolite Substances 0.000 abstract description 10
- 102000004190 Enzymes Human genes 0.000 abstract description 5
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- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 abstract description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 30
- 239000003814 drug Substances 0.000 description 29
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- 239000000243 solution Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 19
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 108090000604 Hydrolases Proteins 0.000 description 7
- 102000004157 Hydrolases Human genes 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000008030 elimination Effects 0.000 description 7
- 238000003379 elimination reaction Methods 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 108090000371 Esterases Proteins 0.000 description 5
- 230000009471 action Effects 0.000 description 5
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- 150000002632 lipids Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
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- 238000006731 degradation reaction Methods 0.000 description 4
- 206010015037 epilepsy Diseases 0.000 description 4
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- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 4
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940125681 anticonvulsant agent Drugs 0.000 description 3
- FTOAOBMCPZCFFF-UHFFFAOYSA-N barbitone sodium Natural products CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 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
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Classifications
-
- 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)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2404898A1 true CA2404898A1 (en) | 2001-11-01 |
Family
ID=22736404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002404898A Abandoned CA2404898A1 (en) | 2000-04-24 | 2001-04-24 | Ultrashort acting hypnotic barbiturates |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6387914B2 (enExample) |
| EP (1) | EP1276728A2 (enExample) |
| JP (1) | JP2003531196A (enExample) |
| AU (2) | AU5723001A (enExample) |
| CA (1) | CA2404898A1 (enExample) |
| WO (1) | WO2001081319A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1276728A2 (en) * | 2000-04-24 | 2003-01-22 | ARYx Therapeutics | Ultrashort acting hypnotic barbiturates |
| US7049326B2 (en) * | 2000-05-12 | 2006-05-23 | The University Of Toledo | Method and compositions for temporarily incapacitating subjects |
| 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 |
| US6750238B1 (en) * | 2000-05-12 | 2004-06-15 | The University Of Toledo | Aralkyl ester soft drugs |
| 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 |
| EP3247359A4 (en) | 2015-01-25 | 2018-08-08 | 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2405732A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Ekto- und endoparasitenmittel |
| CS176667B1 (enExample) * | 1975-02-17 | 1977-06-30 | ||
| IL73840A (en) * | 1983-12-19 | 1988-11-15 | Uniroyal Chem Co Inc | 2-thio-5-(thio)carbamoyl barbituric acid derivatives,their preparation and pharmaceutical compositions containing them |
| DE69032871T2 (de) * | 1989-11-14 | 1999-09-09 | Sloan-Kettering Institute For Cancer Research | Neue potente induktoren terminaler differenzierung und verfahren zu ihrer verwendung |
| CH678394A5 (enExample) * | 1990-08-22 | 1991-09-13 | Cerny Erich H | |
| US5414085A (en) * | 1992-04-06 | 1995-05-09 | Biosite Diagnostics, Inc. | Barbiturate derivatives and protein and polypeptide barbiturate derivative conjugates and labels |
| 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 |
| US6335332B1 (en) * | 1997-06-21 | 2002-01-01 | Roche Diagnostics Gmbh | Barbituric acid derivatives with antimetastatic and antitumor activity |
| EP1276728A2 (en) * | 2000-04-24 | 2003-01-22 | ARYx Therapeutics | Ultrashort acting hypnotic barbiturates |
-
2001
- 2001-04-24 EP EP01930722A patent/EP1276728A2/en not_active Withdrawn
- 2001-04-24 US US09/841,738 patent/US6387914B2/en not_active Expired - Fee Related
- 2001-04-24 WO PCT/US2001/013246 patent/WO2001081319A2/en not_active Ceased
- 2001-04-24 CA CA002404898A patent/CA2404898A1/en not_active Abandoned
- 2001-04-24 JP JP2001578413A patent/JP2003531196A/ja active Pending
- 2001-04-24 AU AU5723001A patent/AU5723001A/xx active Pending
- 2001-04-24 AU AU2001257230A patent/AU2001257230B2/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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003531196A (ja) | 2003-10-21 |
| USRE41289E1 (en) | 2010-04-27 |
| WO2001081319A2 (en) | 2001-11-01 |
| AU5723001A (en) | 2001-11-07 |
| US20030100575A1 (en) | 2003-05-29 |
| US6387914B2 (en) | 2002-05-14 |
| US7041673B2 (en) | 2006-05-09 |
| US6683086B2 (en) | 2004-01-27 |
| AU2001257230B2 (en) | 2006-09-14 |
| WO2001081319A3 (en) | 2002-05-16 |
| US20040167143A1 (en) | 2004-08-26 |
| EP1276728A2 (en) | 2003-01-22 |
| US20020013330A1 (en) | 2002-01-31 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |