CA2510167C - Derivatives of asimadoline with covalently bonded acids - Google Patents
Derivatives of asimadoline with covalently bonded acids Download PDFInfo
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- CA2510167C CA2510167C CA2510167A CA2510167A CA2510167C CA 2510167 C CA2510167 C CA 2510167C CA 2510167 A CA2510167 A CA 2510167A CA 2510167 A CA2510167 A CA 2510167A CA 2510167 C CA2510167 C CA 2510167C
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- Prior art keywords
- acid
- compound
- salt
- pain
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- 239000002253 acid Substances 0.000 title claims abstract description 105
- 150000007513 acids Chemical class 0.000 title claims abstract description 32
- JHLHNYVMZCADTC-LOSJGSFVSA-N asimadoline Chemical class C([C@@H](N(C)C(=O)C(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 JHLHNYVMZCADTC-LOSJGSFVSA-N 0.000 title claims description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 77
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
- 239000012453 solvate Substances 0.000 claims abstract description 42
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- 208000033808 peripheral neuropathy Diseases 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 31
- 238000011321 prophylaxis Methods 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
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- 239000004480 active ingredient Substances 0.000 claims description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
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- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims description 6
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- CGOWXHFQLCCWBS-RRPNLBNLSA-N [(3s)-1-[(2s)-2-[(2,2-diphenylacetyl)-methylamino]-2-phenylethyl]pyrrolidin-3-yl] acetate Chemical compound C([C@@H](N(C)C(=O)C(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)N1CC[C@H](OC(C)=O)C1 CGOWXHFQLCCWBS-RRPNLBNLSA-N 0.000 claims description 4
- DLNKOYKMWOXYQA-IONNQARKSA-N cathine Chemical compound C[C@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-IONNQARKSA-N 0.000 claims description 4
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical group OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 3
- WZLQYDXACAEGQZ-UHFFFAOYSA-N 6-[1-[2-[(2,2-diphenylacetyl)-methylamino]-2-phenylethyl]pyrrolidin-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)N(C)C(C=1C=CC=CC=1)CN(C1)CCC1OC1OC(C(O)=O)C(O)C(O)C1O WZLQYDXACAEGQZ-UHFFFAOYSA-N 0.000 claims description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 2
- XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 claims description 2
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- 229960002179 ephedrine Drugs 0.000 claims description 2
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims description 2
- 229960000395 phenylpropanolamine Drugs 0.000 claims description 2
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 2
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- 210000001635 urinary tract Anatomy 0.000 claims 6
- 239000003402 opiate agonist Substances 0.000 claims 2
- CTLFFPUDXQSXAK-UHFFFAOYSA-N [1-[2-[(2,2-diphenylacetyl)-methylamino]-2-phenylethyl]pyrrolidin-3-yl] hydrogen sulfate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)N(C)C(C=1C=CC=CC=1)CN1CCC(OS(O)(=O)=O)C1 CTLFFPUDXQSXAK-UHFFFAOYSA-N 0.000 claims 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
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- -1 araliphatic Chemical group 0.000 description 31
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000007824 polyneuropathy Effects 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 229960001052 streptozocin Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10259245A DE10259245A1 (de) | 2002-12-17 | 2002-12-17 | Derivate des Asimadolins mit kovalent gebundenen Säuren |
| DE10259245.4 | 2002-12-17 | ||
| PCT/EP2003/013206 WO2004054970A1 (de) | 2002-12-17 | 2003-11-25 | Derivate des asimadolins mit kovalent gebundenen säuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2510167A1 CA2510167A1 (en) | 2004-07-01 |
| CA2510167C true CA2510167C (en) | 2011-05-24 |
Family
ID=32403913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2510167A Expired - Fee Related CA2510167C (en) | 2002-12-17 | 2003-11-25 | Derivatives of asimadoline with covalently bonded acids |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US7385065B2 (enExample) |
| EP (1) | EP1572640B1 (enExample) |
| JP (2) | JP5253709B2 (enExample) |
| AU (1) | AU2003288159B2 (enExample) |
| CA (1) | CA2510167C (enExample) |
| CY (1) | CY1113781T1 (enExample) |
| DE (1) | DE10259245A1 (enExample) |
| DK (1) | DK1572640T3 (enExample) |
| ES (1) | ES2401876T3 (enExample) |
| PE (1) | PE20040910A1 (enExample) |
| PT (1) | PT1572640E (enExample) |
| SI (1) | SI1572640T1 (enExample) |
| TW (1) | TWI335815B (enExample) |
| WO (1) | WO2004054970A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10259245A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | Derivate des Asimadolins mit kovalent gebundenen Säuren |
| US20080090859A1 (en) * | 2003-10-30 | 2008-04-17 | Tioga Pharmaceuticals, Inc. | Use of Selective Opiate Receptor Modulators In the Treatment Of Neuropathy |
| PL2136801T3 (pl) | 2007-03-30 | 2013-01-31 | Tioga Pharmaceuticals Inc | Agoniści kappa-opioidów do leczenia zespołu jelita drażliwego w postaci zmiennej i z dominującą biegunką |
| US9815824B2 (en) | 2013-06-28 | 2017-11-14 | Nektar Therapeutics | Kappa opioid agonists and uses thereof |
| WO2018119108A1 (en) | 2016-12-21 | 2018-06-28 | Tioga Pharmaceuticals Inc. | Splid pharmaceutical formulations of asimadoline |
| WO2019122361A1 (en) * | 2017-12-22 | 2019-06-27 | Dr. August Wolff Gmbh & Co. Kg Arzneimittel | Asimadoline for use in treating pulmonary diseases, vascular diseases, and sepsis |
| EP3932390A1 (en) | 2020-07-02 | 2022-01-05 | Dr. August Wolff GmbH & Co. KG Arzneimittel | Topical gel formulation containing asimadoline |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4889860A (en) | 1985-09-23 | 1989-12-26 | Nova Pharmaceutical Corporation | Oximes of oxymorphone, naltrexone and naloxone as potent, selective opioid receptor agonists and antagonists |
| US4760069A (en) | 1985-09-23 | 1988-07-26 | Nova Pharmaceutical Corporation | Oximes of oxymorphone, naltrexone and naloxone as potent, selective opioid receptor agonists and antagonists |
| US5300687A (en) | 1991-07-18 | 1994-04-05 | Ortho Pharmaceutical Corporation | Trifluoromethylbenzylphosphonates useful in treating osteoporosis |
| DE4215213A1 (de) * | 1992-05-09 | 1993-11-11 | Merck Patent Gmbh | Arylacetamide |
| DE4425071C2 (de) | 1994-07-15 | 1996-08-29 | Degussa | Verfahren zur Herstellung optisch aktiver Pyrrolidine mit hoher Enantiomerenreinheit |
| DE19523502A1 (de) | 1995-06-28 | 1997-01-02 | Merck Patent Gmbh | Kappa-Opiatagonisten für entzündliche Darmerkrankungen |
| DE19531464A1 (de) | 1995-08-26 | 1997-02-27 | Merck Patent Gmbh | N-Methyl-N-[(1S-)-1-phenyl-2-((3S)-3-hydroxypyrrolidin 1-yl-)-ethyl]-2,2-diphenyl-acetamid |
| US6303611B1 (en) | 1996-03-08 | 2001-10-16 | Adolor Corporation | Kappa agonist compounds and pharmaceutical formulations thereof |
| DE19647538A1 (de) | 1996-11-16 | 1998-05-20 | Merck Patent Gmbh | Verfahren zur Herstellung von enantiomerenreinem N-Methyl-N-[1-phenyl-2-(-3-hydroxypyrrolidin-1-yl)ethyl]-2,2-diphenylacetamid |
| US6191126B1 (en) * | 1996-12-16 | 2001-02-20 | Alcon Laboratories, Inc. | Topical use of κ opioid agonists to treat ocular pain |
| PL341762A1 (en) | 1997-12-24 | 2001-05-07 | Vertex Pharma | Precursors of aspartil protease inhibitors |
| DE19827633A1 (de) | 1998-04-20 | 1999-10-21 | Merck Patent Gmbh | Verfahren zur Herstellung von enantiomerenreinem N-Methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)ethyl]-2,2-diphenylacetamid |
| DE19849650A1 (de) | 1998-10-29 | 2000-05-04 | Merck Patent Gmbh | Kappa-Opiatagonisten für die Behandlung des Irritable Bowel Syndroms (IBS) |
| GB0015562D0 (en) | 2000-06-23 | 2000-08-16 | Pfizer Ltd | Heterocycles |
| US20020025948A1 (en) | 2000-06-23 | 2002-02-28 | Banks Bernard Joseph | 3-azabicyclo[3.1.0]hexane derivatives useful in therapy |
| US6846831B2 (en) | 2000-08-15 | 2005-01-25 | Cpd, Llc | Method of treating the syndrome of lipodystrophy |
| US6262062B1 (en) | 2000-08-15 | 2001-07-17 | Cpd, Llc | Method of treating the syndrome of coronary heart disease risk factors in humans |
| US6569449B1 (en) | 2000-11-13 | 2003-05-27 | University Of Kentucky Research Foundation | Transdermal delivery of opioid antagonist prodrugs |
| RU2756946C2 (ru) * | 2001-01-26 | 2021-10-07 | Мерк Шарп И Доум Корп. | Применение замещенных азетидинонов для лечения ситостеролемии |
| DE10116978A1 (de) * | 2001-04-05 | 2002-10-10 | Merck Patent Gmbh | Kappa-Opiatagonisten für die Behandlung von Erkrankungen der Blase |
| US6780891B2 (en) | 2001-11-30 | 2004-08-24 | Sepracor Inc. | Tramadol analogs and uses thereof |
| US20050176746A1 (en) | 2002-05-17 | 2005-08-11 | Frank Weber | Use of compounds that are effective as selective opiate receptor modulators |
| DE10259245A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | Derivate des Asimadolins mit kovalent gebundenen Säuren |
-
2002
- 2002-12-17 DE DE10259245A patent/DE10259245A1/de not_active Withdrawn
-
2003
- 2003-11-25 US US10/539,256 patent/US7385065B2/en not_active Expired - Fee Related
- 2003-11-25 PT PT37800430T patent/PT1572640E/pt unknown
- 2003-11-25 JP JP2004559717A patent/JP5253709B2/ja not_active Expired - Fee Related
- 2003-11-25 EP EP03780043A patent/EP1572640B1/de not_active Expired - Lifetime
- 2003-11-25 WO PCT/EP2003/013206 patent/WO2004054970A1/de not_active Ceased
- 2003-11-25 CA CA2510167A patent/CA2510167C/en not_active Expired - Fee Related
- 2003-11-25 ES ES03780043T patent/ES2401876T3/es not_active Expired - Lifetime
- 2003-11-25 SI SI200332242T patent/SI1572640T1/sl unknown
- 2003-11-25 DK DK03780043.0T patent/DK1572640T3/da active
- 2003-11-25 AU AU2003288159A patent/AU2003288159B2/en not_active Ceased
- 2003-12-10 PE PE2003001254A patent/PE20040910A1/es not_active Application Discontinuation
- 2003-12-11 TW TW092135046A patent/TWI335815B/zh not_active IP Right Cessation
-
2007
- 2007-04-02 US US11/732,309 patent/US20070179098A1/en not_active Abandoned
-
2008
- 2008-06-02 US US12/131,836 patent/US7915228B2/en not_active Expired - Fee Related
-
2011
- 2011-03-31 JP JP2011079933A patent/JP2011157375A/ja active Pending
-
2013
- 2013-02-04 CY CY20131100097T patent/CY1113781T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200418459A (en) | 2004-10-01 |
| ES2401876T3 (es) | 2013-04-25 |
| CY1113781T1 (el) | 2016-07-27 |
| SI1572640T1 (sl) | 2013-03-29 |
| AU2003288159A1 (en) | 2004-07-09 |
| TWI335815B (en) | 2011-01-11 |
| US20060122255A1 (en) | 2006-06-08 |
| DE10259245A1 (de) | 2004-07-01 |
| PE20040910A1 (es) | 2004-12-02 |
| US7915228B2 (en) | 2011-03-29 |
| PT1572640E (pt) | 2013-02-15 |
| JP2011157375A (ja) | 2011-08-18 |
| US7385065B2 (en) | 2008-06-10 |
| EP1572640A1 (de) | 2005-09-14 |
| US20070179098A1 (en) | 2007-08-02 |
| JP5253709B2 (ja) | 2013-07-31 |
| JP2006511521A (ja) | 2006-04-06 |
| AU2003288159B2 (en) | 2010-05-20 |
| WO2004054970A1 (de) | 2004-07-01 |
| HK1080479A1 (en) | 2006-04-28 |
| US20080234209A1 (en) | 2008-09-25 |
| EP1572640B1 (de) | 2012-11-07 |
| DK1572640T3 (da) | 2013-02-11 |
| CA2510167A1 (en) | 2004-07-01 |
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