DE10224624A1 - Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol - Google Patents
Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-olInfo
- Publication number
- DE10224624A1 DE10224624A1 DE10224624A DE10224624A DE10224624A1 DE 10224624 A1 DE10224624 A1 DE 10224624A1 DE 10224624 A DE10224624 A DE 10224624A DE 10224624 A DE10224624 A DE 10224624A DE 10224624 A1 DE10224624 A1 DE 10224624A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- stereoisomers
- salts
- dimethylamino
- alkyl
- 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.)
- Withdrawn
Links
- PZNRRUTVGXCKFC-UHFFFAOYSA-N 1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)CC(C)C(O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-UHFFFAOYSA-N 0.000 title claims description 9
- 239000002207 metabolite Substances 0.000 title claims description 8
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 21
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 18
- 206010027566 Micturition urgency Diseases 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 16
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 16
- -1 cycloalkyl radicals Chemical class 0.000 description 35
- 235000002639 sodium chloride Nutrition 0.000 description 29
- 210000003932 urinary bladder Anatomy 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000000126 substance Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000027939 micturition Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 238000009472 formulation Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- PZNRRUTVGXCKFC-IUODEOHRSA-N (2r,3r)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)C[C@@H](C)[C@](O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-IUODEOHRSA-N 0.000 description 3
- PZNRRUTVGXCKFC-WFASDCNBSA-N (2s,3s)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol Chemical compound CN(C)C[C@H](C)[C@@](O)(CC)C1=CC=CC(OC)=C1 PZNRRUTVGXCKFC-WFASDCNBSA-N 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
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- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 2
- VIKBNMWOLLIQPG-UHFFFAOYSA-N 2-methyldecanedioic acid Chemical compound OC(=O)C(C)CCCCCCCC(O)=O VIKBNMWOLLIQPG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- INCYIBYTUZLVLV-UHFFFAOYSA-N 3-[1-(dimethylamino)-3-hydroxy-2-methylpentan-3-yl]phenol Chemical compound CN(C)CC(C)C(O)(CC)C1=CC=CC(O)=C1 INCYIBYTUZLVLV-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 2
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- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/72—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with quaternised amino groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10224624A DE10224624A1 (de) | 2002-05-30 | 2002-05-30 | Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol |
| AU2003238398A AU2003238398A1 (en) | 2002-05-30 | 2003-05-26 | Metabolite of 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentane-3-ol and the use thereof in the treatment of urinary incontinence |
| EP03732465A EP1507521A1 (de) | 2002-05-30 | 2003-05-26 | Metabolite von 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol sowie deren verwendung zur behandlung von harninkontinenz |
| PCT/EP2003/005490 WO2003101440A1 (de) | 2002-05-30 | 2003-05-26 | Metabolite von 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol sowie deren verwendung zur behandlung von harninkontinenz |
| PE2003000510A PE20040521A1 (es) | 2002-05-30 | 2003-05-27 | Metabolito a partir de 1-dimetilamino-3-(3-metoxi-fenil)-2-metil-pentan-3-ol |
| ARP030101885A AR039901A1 (es) | 2002-05-30 | 2003-05-29 | Metabolito a partir de 1-dimetilamino-3-(3-metoxi-fenil)-2-metil-pentan-3-ol |
| US10/999,219 US20050137145A1 (en) | 2002-05-30 | 2004-11-30 | Metabolites of 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol and their use in the treatment of urinary incontinence |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10224624A DE10224624A1 (de) | 2002-05-30 | 2002-05-30 | Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10224624A1 true DE10224624A1 (de) | 2003-12-11 |
Family
ID=29432607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10224624A Withdrawn DE10224624A1 (de) | 2002-05-30 | 2002-05-30 | Metabolite und Prodrugs von 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1507521A1 (es) |
| AR (1) | AR039901A1 (es) |
| AU (1) | AU2003238398A1 (es) |
| DE (1) | DE10224624A1 (es) |
| PE (1) | PE20040521A1 (es) |
| WO (1) | WO2003101440A1 (es) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| WO2002043715A2 (de) * | 2000-11-30 | 2002-06-06 | Grünenthal GmbH | Verwendung von 1-phenyl-3-dimethylamino-propanverbindungen zur therapie der harninkontinenz |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901180A1 (de) * | 1979-01-13 | 1980-07-24 | Basf Ag | Hexahydro-1,4-oxazepine, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| PE20010623A1 (es) * | 1999-10-05 | 2001-07-07 | Gruenenthal Chemie | Uso de (+)-tramadol y/o o-demetiltramadol para tratamiento de urgencia urinaria incrementada y/o incontinencia urinaria |
-
2002
- 2002-05-30 DE DE10224624A patent/DE10224624A1/de not_active Withdrawn
-
2003
- 2003-05-26 EP EP03732465A patent/EP1507521A1/de not_active Withdrawn
- 2003-05-26 AU AU2003238398A patent/AU2003238398A1/en not_active Abandoned
- 2003-05-26 WO PCT/EP2003/005490 patent/WO2003101440A1/de not_active Ceased
- 2003-05-27 PE PE2003000510A patent/PE20040521A1/es not_active Application Discontinuation
- 2003-05-29 AR ARP030101885A patent/AR039901A1/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| WO2002043715A2 (de) * | 2000-11-30 | 2002-06-06 | Grünenthal GmbH | Verwendung von 1-phenyl-3-dimethylamino-propanverbindungen zur therapie der harninkontinenz |
Also Published As
| Publication number | Publication date |
|---|---|
| PE20040521A1 (es) | 2004-08-24 |
| WO2003101440A1 (de) | 2003-12-11 |
| AU2003238398A1 (en) | 2003-12-19 |
| EP1507521A1 (de) | 2005-02-23 |
| AR039901A1 (es) | 2005-03-09 |
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| 8139 | Disposal/non-payment of the annual fee |