JP2009539777A5 - - Google Patents
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- Publication number
- JP2009539777A5 JP2009539777A5 JP2009513524A JP2009513524A JP2009539777A5 JP 2009539777 A5 JP2009539777 A5 JP 2009539777A5 JP 2009513524 A JP2009513524 A JP 2009513524A JP 2009513524 A JP2009513524 A JP 2009513524A JP 2009539777 A5 JP2009539777 A5 JP 2009539777A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- trimebutine
- nitroarginine
- demethylated
- pain
- 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.)
- Granted
Links
- LORDFXWUHHSAQU-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid [2-(dimethylamino)-2-phenylbutyl] ester Chemical compound C=1C=CC=CC=1C(CC)(N(C)C)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 LORDFXWUHHSAQU-UHFFFAOYSA-N 0.000 claims description 19
- 229960005345 trimebutine Drugs 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- 208000004998 Abdominal Pain Diseases 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 208000009935 visceral pain Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 28
- UMWBHGDTJNLDHJ-VWMHFEHESA-N (2S)-5-(diaminomethylideneamino)-2-nitramidopentanoic acid 4-hydroxybenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(O)C=C1.NC(=N)NCCC[C@@H](C(O)=O)N[N+]([O-])=O UMWBHGDTJNLDHJ-VWMHFEHESA-N 0.000 claims 2
- IGDGSQZPIWOEGV-UHFFFAOYSA-N 2-carbamothioylbenzoic acid Chemical compound NC(=S)C1=CC=CC=C1C(O)=O IGDGSQZPIWOEGV-UHFFFAOYSA-N 0.000 claims 2
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- GVEVKAIAOIRIAL-UHFFFAOYSA-N 4-carbamothioylbenzoic acid Chemical compound NC(=S)C1=CC=C(C(O)=O)C=C1 GVEVKAIAOIRIAL-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- 206010051153 Diabetic gastroparesis Diseases 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 16
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 102000016924 KATP Channels Human genes 0.000 description 2
- 108010053914 KATP Channels Proteins 0.000 description 2
- 102000008212 P-Selectin Human genes 0.000 description 2
- 108010035766 P-Selectin Proteins 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 239000000050 smooth muscle relaxant Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- JYNPQXKLKQHEFP-UHFFFAOYSA-N CCCCC1(C(C(=C(C(=C1C)C)C)NC)C(=O)O)C2=CC=CC=C2 Chemical compound CCCCC1(C(C(=C(C(=C1C)C)C)NC)C(=O)O)C2=CC=CC=C2 JYNPQXKLKQHEFP-UHFFFAOYSA-N 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FSRLGULMGJGKGI-BTJKTKAUSA-N Trimebutine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=CC=1C(CC)(N(C)C)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 FSRLGULMGJGKGI-BTJKTKAUSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 230000007248 cellular mechanism Effects 0.000 description 1
- 239000005482 chemotactic factor Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 210000003989 endothelium vascular Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000008991 intestinal motility Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000023404 leukocyte cell-cell adhesion Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000007658 neurological function Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000003488 releasing hormone Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 1
- 229960001661 ursodiol Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80406706P | 2006-06-06 | 2006-06-06 | |
| US60/804,067 | 2006-06-06 | ||
| PCT/CA2007/001008 WO2007140611A1 (en) | 2006-06-06 | 2007-06-06 | Salts of trimebutine and n-desmethyl trimebutine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009539777A JP2009539777A (ja) | 2009-11-19 |
| JP2009539777A5 true JP2009539777A5 (https=) | 2010-12-24 |
| JP5421098B2 JP5421098B2 (ja) | 2014-02-19 |
Family
ID=38801016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009513524A Expired - Fee Related JP5421098B2 (ja) | 2006-06-06 | 2007-06-06 | トリメブチン及びｎ−脱メチル化トリメブチンの塩類 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7666907B2 (https=) |
| EP (1) | EP2024323B1 (https=) |
| JP (1) | JP5421098B2 (https=) |
| KR (1) | KR20090021346A (https=) |
| CN (1) | CN101489986A (https=) |
| AU (1) | AU2007257174B2 (https=) |
| BR (1) | BRPI0712417A2 (https=) |
| CA (1) | CA2653869A1 (https=) |
| RU (1) | RU2008152751A (https=) |
| WO (1) | WO2007140611A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7741359B2 (en) * | 2005-05-27 | 2010-06-22 | Antibe Therapeutics Inc. | Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs |
| US7932286B2 (en) * | 2007-07-31 | 2011-04-26 | Martin Francois | Method for treating colonic viscerosensitivity and spasticity |
| FR2927076B1 (fr) * | 2008-01-31 | 2010-03-26 | Oroxcell | Derives de 2-amino-2-phenyl-alkanol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| CA2827887C (en) * | 2011-08-15 | 2020-06-09 | Research Foundation Of The City University Of New York | No- and h2s-releasing compounds |
| RU2014138619A (ru) * | 2012-03-12 | 2016-05-10 | Джикеа Фарма Инк. | Новые соли тримебутина на основе сульфонатов |
| JP2017528505A (ja) | 2014-09-25 | 2017-09-28 | ザ・ホスピタル・フォー・シック・チルドレンＴｈｅ Ｈｏｓｐｉｔａｌ Ｆｏｒ Ｓｉｃｋ Ｃｈｉｌｄｒｅｎ | 発毛増進、皮膚再生促進及び創傷治癒のための組成物及び方法 |
| RU2752086C1 (ru) * | 2020-04-27 | 2021-07-22 | Общество С Ограниченной Ответственностью "Валента-Интеллект" | Новое соединение [2-(диметиламино)-2-фенилбутил]-3,4,5-триметоксибензоата 4-метил-2н-хромен-2-он-7-илсульфат и его применение |
| CN114190383B (zh) * | 2021-12-06 | 2022-09-06 | 南京天秾生物技术有限公司 | 2-氨基-3-苯基丁酸或2,6-二氨基-3-甲基己酸作为植物免疫诱抗剂的应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460919A1 (fr) * | 1979-07-11 | 1981-01-30 | Prod Synthese Ste Indle | Amino-ethers oxydes, leur procede de preparation et leur application en therapeutique |
| JPS57500432A (https=) * | 1980-03-20 | 1982-03-11 | ||
| US4412992A (en) * | 1980-07-21 | 1983-11-01 | Biorex Laboratories Limited | 2-Hydroxy-5-phenylazobenzoic acid derivatives and method of treating ulcerative colitis therewith |
| US4440763A (en) * | 1981-03-18 | 1984-04-03 | Block Drug Company, Inc. | Use of 4-aminosalicyclic acid as an anti-inflammatory agent |
| ZA825384B (en) * | 1981-07-31 | 1983-05-25 | Tillott J B Ltd | Orally administrable pharmaceutical compositions |
| US4751221A (en) * | 1985-10-18 | 1988-06-14 | Sloan-Kettering Institute For Cancer Research | 2-fluoro-arabinofuranosyl purine nucleosides |
| US5245080A (en) * | 1989-02-20 | 1993-09-14 | Jouveinal Sa | (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine, process for preparing it and its therapeutical use |
| US5811547A (en) * | 1992-10-14 | 1998-09-22 | Nippon Shinyaju Co., Ltd. | Method for inducing crystalline state transition in medicinal substance |
| WO1997009329A1 (en) | 1995-09-08 | 1997-03-13 | J. Uriach & Cia. S.A. | Azo derivatives of 5-aminosalicylic acid for treatment of inflammatory bowel disease |
| SE9700934D0 (sv) * | 1997-03-14 | 1997-03-14 | Astra Ab | New formulation |
| AU7246398A (en) * | 1997-04-30 | 1998-11-24 | Northwestern University | Inhibition of nitric oxide synthase by amino acids and dipeptides |
| EP1110549A1 (en) * | 1999-12-23 | 2001-06-27 | Warner-Lambert Company | Use of trimebutine for treating pain |
| SV2001000242A (es) * | 1999-12-23 | 2001-10-25 | Warner Lambert Co | Combinacion de trimebutina con un analgesico derivado del opio |
| JP2003532703A (ja) * | 2000-05-05 | 2003-11-05 | ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーション・シヤンテイフイツク・（エス．セー．エール．アー．エス） | 新規アミノ酸誘導体及びその医薬としての使用 |
| AU2001279064A1 (en) * | 2000-07-27 | 2002-02-13 | Rutgers, The State University | Therapeutic azo-compounds for drug delivery |
| ATE460394T1 (de) * | 2000-08-29 | 2010-03-15 | Biocon Ltd | 5-asa-derivate mit entzündungshemmender und antibiotischer wirkung und verfahren zur behandlung von krankheiten mit diesen derivaten |
| BR0312501A (pt) * | 2002-07-10 | 2005-04-12 | Warner Lambert Co | Combinação de um inibidor alostérico ou metaloproteinase de matriz-13 com um inibidor de ciclooxigenase-2 diferente de celecoxib ou valdecoxib |
| US6986901B2 (en) * | 2002-07-15 | 2006-01-17 | Warner-Lambert Company Llc | Gastrointestinal compositions |
| WO2004066987A2 (en) * | 2003-01-30 | 2004-08-12 | Dynogen Pharmaceuticals, Inc. | Use of sodium channel modulators for treating gastrointestinal tract disorders |
| EP1886681A3 (en) | 2004-10-07 | 2008-11-19 | Sulfidris S.r.l. | 5-(p-hydroxyphenyl)-3H-1,2-dithiol-3-thione valproate ester |
-
2007
- 2007-06-06 US US11/759,154 patent/US7666907B2/en not_active Expired - Fee Related
- 2007-06-06 CA CA002653869A patent/CA2653869A1/en not_active Abandoned
- 2007-06-06 JP JP2009513524A patent/JP5421098B2/ja not_active Expired - Fee Related
- 2007-06-06 US US12/303,082 patent/US20110144188A1/en not_active Abandoned
- 2007-06-06 BR BRPI0712417-1A patent/BRPI0712417A2/pt not_active IP Right Cessation
- 2007-06-06 EP EP07719924A patent/EP2024323B1/en not_active Not-in-force
- 2007-06-06 WO PCT/CA2007/001008 patent/WO2007140611A1/en not_active Ceased
- 2007-06-06 CN CNA2007800264544A patent/CN101489986A/zh active Pending
- 2007-06-06 AU AU2007257174A patent/AU2007257174B2/en not_active Ceased
- 2007-06-06 KR KR1020087029794A patent/KR20090021346A/ko not_active Withdrawn
- 2007-06-06 RU RU2008152751/04A patent/RU2008152751A/ru unknown
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