CA2630222A1 - Carbamate compounds as 5-ht4 receptor agonists - Google Patents
Carbamate compounds as 5-ht4 receptor agonists Download PDFInfo
- Publication number
- CA2630222A1 CA2630222A1 CA002630222A CA2630222A CA2630222A1 CA 2630222 A1 CA2630222 A1 CA 2630222A1 CA 002630222 A CA002630222 A CA 002630222A CA 2630222 A CA2630222 A CA 2630222A CA 2630222 A1 CA2630222 A1 CA 2630222A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- isopropyl
- 3alkyl
- carbonyl
- 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
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- 239000000018 receptor agonist Substances 0.000 title abstract description 17
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- 238000000034 method Methods 0.000 claims abstract description 74
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- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 238000012353 t test Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- NZJKEPNCNBWESN-PBINXNQUSA-N tert-butyl (1s,5r)-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(N)C[C@H]2CC[C@@H]1N2C(=O)OC(C)(C)C NZJKEPNCNBWESN-PBINXNQUSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 210000001578 tight junction Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
-
- 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
-
- 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
- A61P1/10—Laxatives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73870205P | 2005-11-22 | 2005-11-22 | |
| US60/738,702 | 2005-11-22 | ||
| PCT/US2006/045099 WO2007062058A2 (en) | 2005-11-22 | 2006-11-21 | Carbamate compounds as 5-ht4 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2630222A1 true CA2630222A1 (en) | 2007-05-31 |
Family
ID=38067868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002630222A Abandoned CA2630222A1 (en) | 2005-11-22 | 2006-11-21 | Carbamate compounds as 5-ht4 receptor agonists |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7329752B2 (https=) |
| EP (1) | EP1960396B1 (https=) |
| JP (1) | JP2009516745A (https=) |
| KR (1) | KR20080072727A (https=) |
| CN (1) | CN101312967B (https=) |
| AR (1) | AR057627A1 (https=) |
| AT (1) | ATE448224T1 (https=) |
| AU (1) | AU2006318507A1 (https=) |
| BR (1) | BRPI0618835A2 (https=) |
| CA (1) | CA2630222A1 (https=) |
| DE (1) | DE602006010432D1 (https=) |
| EA (1) | EA014819B1 (https=) |
| ES (1) | ES2336952T3 (https=) |
| MY (1) | MY143574A (https=) |
| NO (1) | NO20082597L (https=) |
| NZ (1) | NZ567653A (https=) |
| PE (1) | PE20070954A1 (https=) |
| TW (1) | TW200804366A (https=) |
| WO (1) | WO2007062058A2 (https=) |
| ZA (1) | ZA200804010B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101163701A (zh) * | 2005-03-02 | 2008-04-16 | 施万制药 | 作为5-ht4受体激动剂的喹啉酮化合物 |
| CN101384588B (zh) * | 2006-02-16 | 2011-08-31 | 施万制药 | 制备5-ht4受体激动剂化合物的中间体的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223511A (en) | 1987-09-23 | 1993-06-29 | Boehringer Ingelheim Italia S.P.A. | Benzimidazoline-2-oxo-1-carboxylic acid compounds useful as 5-HT receptor antagonists |
| IT1231413B (it) | 1987-09-23 | 1991-12-04 | Angeli Inst Spa | Derivati dell'acido benzimidazolin-2-osso-1-carbossilico utili come antagonisti dei recettori 5-ht |
| JP3829879B2 (ja) | 1994-05-18 | 2006-10-04 | 大正製薬株式会社 | キノリンカルボン酸誘導体 |
| IT1275903B1 (it) | 1995-03-14 | 1997-10-24 | Boehringer Ingelheim Italia | Esteri e ammidi della 1,4-piperidina disostituita |
| US6069152A (en) * | 1997-10-07 | 2000-05-30 | Eli Lilly And Company | 5-HT4 agonists and antagonists |
| IT1298271B1 (it) | 1998-02-18 | 1999-12-20 | Boehringer Ingelheim Italia | Esteri ed ammidi dell'acido 2-oxo-2,3-diidro-benzimidazol-1- carbossilico |
| EP1173168A2 (en) | 1999-04-28 | 2002-01-23 | Respiratorius AB | Compound for use as a medicament for treatment of disorders involving bronchocontraction |
| IT1313625B1 (it) | 1999-09-22 | 2002-09-09 | Boehringer Ingelheim Italia | Derivati benzimidazolonici aventi affinita' mista per i recettori diserotonina e dopamina. |
| JP4181847B2 (ja) * | 2002-10-25 | 2008-11-19 | エルピーダメモリ株式会社 | タイミング調整回路、半導体装置及びタイミング調整方法 |
| KR100738784B1 (ko) | 2003-09-03 | 2007-07-12 | 화이자 인코포레이티드 | 5-ｈｔ4 수용체 효능 활성을 갖는 벤즈이미다졸론 |
| TW200533348A (en) | 2004-02-18 | 2005-10-16 | Theravance Inc | Indazole-carboxamide compounds as 5-ht4 receptor agonists |
| TWI351282B (en) | 2004-04-07 | 2011-11-01 | Theravance Inc | Quinolinone-carboxamide compounds as 5-ht4 recepto |
| WO2006052889A2 (en) * | 2004-11-05 | 2006-05-18 | Theravance, Inc. | Quinolinone-carboxamide compounds |
| US7399862B2 (en) | 2004-11-05 | 2008-07-15 | Theravance, Inc. | 5-HT4 receptor agonist compounds |
| CA2588037A1 (en) | 2004-12-22 | 2006-06-29 | Theravance, Inc. | Indazole-carboxamide compounds |
| CN101163701A (zh) * | 2005-03-02 | 2008-04-16 | 施万制药 | 作为5-ht4受体激动剂的喹啉酮化合物 |
| US7351304B2 (en) * | 2005-05-24 | 2008-04-01 | General Electric Company | Method and apparatus for reducing surface defects |
| EP1902053B1 (en) | 2005-06-07 | 2011-01-12 | Theravance, Inc. | Benzoimidazolone-carboxamide compounds as 5-ht4 receptor agonists |
-
2006
- 2006-11-09 MY MYPI20064472A patent/MY143574A/en unknown
- 2006-11-15 TW TW095142293A patent/TW200804366A/zh unknown
- 2006-11-21 AT AT06838207T patent/ATE448224T1/de not_active IP Right Cessation
- 2006-11-21 DE DE602006010432T patent/DE602006010432D1/de active Active
- 2006-11-21 JP JP2008542415A patent/JP2009516745A/ja active Pending
- 2006-11-21 EP EP06838207A patent/EP1960396B1/en active Active
- 2006-11-21 NZ NZ567653A patent/NZ567653A/en unknown
- 2006-11-21 EA EA200801402A patent/EA014819B1/ru not_active IP Right Cessation
- 2006-11-21 US US11/602,888 patent/US7329752B2/en active Active
- 2006-11-21 WO PCT/US2006/045099 patent/WO2007062058A2/en not_active Ceased
- 2006-11-21 BR BRPI0618835-4A patent/BRPI0618835A2/pt not_active IP Right Cessation
- 2006-11-21 ES ES06838207T patent/ES2336952T3/es active Active
- 2006-11-21 PE PE2006001486A patent/PE20070954A1/es not_active Application Discontinuation
- 2006-11-21 KR KR1020087014898A patent/KR20080072727A/ko not_active Ceased
- 2006-11-21 CN CN2006800433139A patent/CN101312967B/zh not_active Expired - Fee Related
- 2006-11-21 AU AU2006318507A patent/AU2006318507A1/en not_active Abandoned
- 2006-11-21 CA CA002630222A patent/CA2630222A1/en not_active Abandoned
- 2006-11-22 AR ARP060105125A patent/AR057627A1/es not_active Application Discontinuation
-
2007
- 2007-12-06 US US11/999,609 patent/US7851467B2/en not_active Expired - Fee Related
-
2008
- 2008-05-09 ZA ZA200804010A patent/ZA200804010B/xx unknown
- 2008-06-10 NO NO20082597A patent/NO20082597L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7851467B2 (en) | 2010-12-14 |
| EP1960396B1 (en) | 2009-11-11 |
| US20080090811A1 (en) | 2008-04-17 |
| ZA200804010B (en) | 2009-02-25 |
| EA014819B1 (ru) | 2011-02-28 |
| EA200801402A1 (ru) | 2008-10-30 |
| NZ567653A (en) | 2011-06-30 |
| CN101312967A (zh) | 2008-11-26 |
| MY143574A (en) | 2011-05-31 |
| DE602006010432D1 (de) | 2009-12-24 |
| WO2007062058A3 (en) | 2007-09-07 |
| PE20070954A1 (es) | 2007-09-10 |
| AU2006318507A1 (en) | 2007-05-31 |
| US20070117796A1 (en) | 2007-05-24 |
| EP1960396A2 (en) | 2008-08-27 |
| ATE448224T1 (de) | 2009-11-15 |
| NO20082597L (no) | 2008-06-10 |
| ES2336952T3 (es) | 2010-04-19 |
| JP2009516745A (ja) | 2009-04-23 |
| AR057627A1 (es) | 2007-12-05 |
| US7329752B2 (en) | 2008-02-12 |
| CN101312967B (zh) | 2011-08-24 |
| BRPI0618835A2 (pt) | 2011-09-13 |
| WO2007062058A2 (en) | 2007-05-31 |
| TW200804366A (en) | 2008-01-16 |
| KR20080072727A (ko) | 2008-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131121 |