DE2710242A1 - 5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungen - Google Patents
5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungenInfo
- Publication number
- DE2710242A1 DE2710242A1 DE19772710242 DE2710242A DE2710242A1 DE 2710242 A1 DE2710242 A1 DE 2710242A1 DE 19772710242 DE19772710242 DE 19772710242 DE 2710242 A DE2710242 A DE 2710242A DE 2710242 A1 DE2710242 A1 DE 2710242A1
- Authority
- DE
- Germany
- Prior art keywords
- azabicyclo
- diphenyl
- propyl7
- hydroxy
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 42
- -1 OCT-2-YL Chemical class 0.000 title description 6
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical class [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 12
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- RLFZYIUUQBHRNV-UHFFFAOYSA-N 2,5-dihydrooxadiazole Chemical compound C1ONN=C1 RLFZYIUUQBHRNV-UHFFFAOYSA-N 0.000 claims 1
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- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/665,609 US4013668A (en) | 1976-03-10 | 1976-03-10 | 5-(1,1-diphenyl-3-(5- or 6-hydroxy-2-azabicyclo(2.2.2)oct-2-yl)propyl)-2-alkyl-1,3,4-oxadiazoles and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2710242A1 true DE2710242A1 (de) | 1977-09-22 |
Family
ID=24670819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772710242 Withdrawn DE2710242A1 (de) | 1976-03-10 | 1977-03-09 | 5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungen |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4013668A (enExample) |
| JP (1) | JPS5951955B2 (enExample) |
| AT (1) | AT350559B (enExample) |
| AU (1) | AU505650B2 (enExample) |
| BE (1) | BE852252A (enExample) |
| CA (1) | CA1078386A (enExample) |
| CH (1) | CH627467A5 (enExample) |
| DE (1) | DE2710242A1 (enExample) |
| DK (1) | DK103777A (enExample) |
| ES (1) | ES456687A1 (enExample) |
| FR (1) | FR2343740A2 (enExample) |
| GB (1) | GB1524653A (enExample) |
| IE (1) | IE44639B1 (enExample) |
| NL (1) | NL7702537A (enExample) |
| NZ (1) | NZ183540A (enExample) |
| SE (1) | SE7702640L (enExample) |
| ZA (1) | ZA771428B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0241180A (ja) * | 1988-07-29 | 1990-02-09 | Shinji Kanda | 耐火避難用カプセル |
| DE69220258T2 (de) * | 1991-02-11 | 1997-12-18 | Merck Sharp & Dohme | Azabicyclische Verbindungen, diese enthaltende pharmazeutische Zubereitungen und ihre therapeutische Verwendung |
| US5962477A (en) * | 1994-04-12 | 1999-10-05 | Adolor Corporation | Screening methods for cytokine inhibitors |
| US6190691B1 (en) | 1994-04-12 | 2001-02-20 | Adolor Corporation | Methods for treating inflammatory conditions |
| US5849761A (en) * | 1995-09-12 | 1998-12-15 | Regents Of The University Of California | Peripherally active anti-hyperalgesic opiates |
| US6573282B1 (en) | 1995-09-12 | 2003-06-03 | Adolor Corporation | Peripherally active anti-hyperalgesic opiates |
| US5667773A (en) * | 1996-03-12 | 1997-09-16 | Adolor Corporation | Film-forming compositions of antihyperalgesic opiates and method of treating hyperalgesic conditions therewith |
| US6353004B1 (en) | 1997-07-14 | 2002-03-05 | Adolor Coporation | Peripherally acting anti-pruritic opiates |
| US20030158220A1 (en) * | 1997-11-03 | 2003-08-21 | Foss Joseph F. | Use of methylnaltrexone and related compounds to treat chronic opioid use side effects |
| PT1615646E (pt) * | 2003-04-08 | 2015-02-12 | Progenics Pharm Inc | Formulações farmacêuticas com metilnaltrexona |
| AR057035A1 (es) | 2005-05-25 | 2007-11-14 | Progenics Pharm Inc | SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS |
| AR057325A1 (es) | 2005-05-25 | 2007-11-28 | Progenics Pharm Inc | Sintesis de (s)-n-metilnaltrexona, composiciones farmaceuticas y usos |
| TWI489984B (zh) | 2006-08-04 | 2015-07-01 | Wyeth Corp | 用於非經腸道傳輸化合物之配方及其用途 |
| TW200817048A (en) * | 2006-09-08 | 2008-04-16 | Wyeth Corp | Dry powder compound formulations and uses thereof |
| PT2565195E (pt) * | 2007-03-29 | 2015-07-28 | Wyeth Llc | Antagonistas e receptor opióide periférico e respectivas utilizações |
| PE20130480A1 (es) | 2007-03-29 | 2013-05-08 | Progenics Pharm Inc | Compuestos heterociclicos como antagonistas del receptor opioide periferico |
| MX2009010550A (es) * | 2007-03-29 | 2009-12-14 | Progenics Pharm Inc | Formas de cristal de bromuro de (r)-n-metilnaltrexona y uso de las mismas. |
| CA2713568C (en) | 2008-02-06 | 2016-09-20 | Progenics Pharmaceuticals, Inc. | Preparation and use of (r),(r)-2,2'-bis-methylnaltrexone |
| WO2010029313A1 (en) * | 2008-09-11 | 2010-03-18 | Summit Corporation Plc. | Antiinfective compounds |
| CA2676881C (en) | 2008-09-30 | 2017-04-25 | Wyeth | Peripheral opioid receptor antagonists and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917615A (en) * | 1974-04-01 | 1975-11-04 | Searle & Co | 1,1-Diaryl-1-oxadiazol-alkylamines |
-
1976
- 1976-03-10 US US05/665,609 patent/US4013668A/en not_active Expired - Lifetime
-
1977
- 1977-03-09 BE BE175614A patent/BE852252A/xx not_active IP Right Cessation
- 1977-03-09 AT AT157477A patent/AT350559B/de not_active IP Right Cessation
- 1977-03-09 CH CH295177A patent/CH627467A5/de not_active IP Right Cessation
- 1977-03-09 NL NL7702537A patent/NL7702537A/xx not_active Application Discontinuation
- 1977-03-09 NZ NZ183540A patent/NZ183540A/xx unknown
- 1977-03-09 IE IE515/77A patent/IE44639B1/en unknown
- 1977-03-09 SE SE7702640A patent/SE7702640L/xx unknown
- 1977-03-09 AU AU23029/77A patent/AU505650B2/en not_active Expired
- 1977-03-09 CA CA273,594A patent/CA1078386A/en not_active Expired
- 1977-03-09 ZA ZA00771428A patent/ZA771428B/xx unknown
- 1977-03-09 DK DK103777A patent/DK103777A/da unknown
- 1977-03-09 ES ES456687A patent/ES456687A1/es not_active Expired
- 1977-03-09 GB GB10031/77A patent/GB1524653A/en not_active Expired
- 1977-03-09 DE DE19772710242 patent/DE2710242A1/de not_active Withdrawn
- 1977-03-09 JP JP52025851A patent/JPS5951955B2/ja not_active Expired
- 1977-03-10 FR FR7707155A patent/FR2343740A2/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK103777A (da) | 1977-09-11 |
| FR2343740A2 (fr) | 1977-10-07 |
| CA1078386A (en) | 1980-05-27 |
| US4013668A (en) | 1977-03-22 |
| IE44639B1 (en) | 1982-02-10 |
| JPS5951955B2 (ja) | 1984-12-17 |
| IE44639L (en) | 1977-09-10 |
| NZ183540A (en) | 1980-05-27 |
| ZA771428B (en) | 1978-10-25 |
| GB1524653A (en) | 1978-09-13 |
| ES456687A1 (es) | 1978-02-01 |
| SE7702640L (sv) | 1977-09-11 |
| CH627467A5 (de) | 1982-01-15 |
| AT350559B (de) | 1979-06-11 |
| JPS52108999A (en) | 1977-09-12 |
| AU2302977A (en) | 1978-09-14 |
| FR2343740B2 (enExample) | 1980-06-20 |
| ATA157477A (de) | 1978-11-15 |
| NL7702537A (nl) | 1977-09-13 |
| AU505650B2 (en) | 1979-11-29 |
| BE852252A (fr) | 1977-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |