MXPA99009120A - (s)2-metilamino-2-fenil-n-butil 3,4,5,-trimetoxibenzoato, sus aplicaciones para el tratamiento del dolor cronico. - Google Patents
(s)2-metilamino-2-fenil-n-butil 3,4,5,-trimetoxibenzoato, sus aplicaciones para el tratamiento del dolor cronico.Info
- Publication number
- MXPA99009120A MXPA99009120A MXPA99009120A MX9909120A MXPA99009120A MX PA99009120 A MXPA99009120 A MX PA99009120A MX PA99009120 A MXPA99009120 A MX PA99009120A MX 9909120 A MX9909120 A MX 9909120A MX PA99009120 A MXPA99009120 A MX PA99009120A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- methylamino
- trimethoxybenzoate
- butyl
- pain
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 208000002193 Pain Diseases 0.000 claims abstract description 33
- ZFPDLGDYDUPYEZ-OAQYLSRUSA-N [(2s)-2-(methylamino)-2-phenylbutyl] 3,4,5-trimethoxybenzoate Chemical compound C([C@@](CC)(NC)C=1C=CC=CC=1)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZFPDLGDYDUPYEZ-OAQYLSRUSA-N 0.000 claims abstract description 19
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- HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 claims 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 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
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- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 1
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- 239000000010 aprotic solvent Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- 210000000013 bile duct Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910010277 boron hydride Inorganic materials 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 208000022371 chronic pain syndrome Diseases 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
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- 238000010586 diagram Methods 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 201000005518 mononeuropathy Diseases 0.000 description 1
- JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 1
- 102000051367 mu Opioid Receptors Human genes 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000003040 nociceptive effect Effects 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
- 230000000631 nonopiate Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 230000007824 polyneuropathy Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003334 secondary amides Chemical group 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 208000037816 tissue injury Diseases 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
- 230000008733 trauma Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9708323A FR2765218B1 (fr) | 1997-06-30 | 1997-06-30 | Le (s) 3,4,5-trimethoxybenzoate de 2-methylamino-2-phenyl-n- butyle, son application au traitement des douleurs chroniques |
| PCT/EP1998/003825 WO1999001417A1 (fr) | 1997-06-30 | 1998-06-23 | (S) 2-METHYLAMINO-2-PHENYL-n-BUTYLE 3,4,5-TRIMETHOXYBENZOATE ET SON UTILISATION DANS LE TRAITEMENT DE LA DOULEUR CHRONIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99009120A true MXPA99009120A (es) | 2005-01-10 |
Family
ID=9508729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA99009120A MXPA99009120A (es) | 1997-06-30 | 1998-06-23 | (s)2-metilamino-2-fenil-n-butil 3,4,5,-trimetoxibenzoato, sus aplicaciones para el tratamiento del dolor cronico. |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0993436A1 (fr) |
| JP (1) | JP2002508776A (fr) |
| KR (1) | KR20010014294A (fr) |
| AU (1) | AU731887B2 (fr) |
| BR (1) | BR9810387A (fr) |
| CA (1) | CA2285479A1 (fr) |
| FR (1) | FR2765218B1 (fr) |
| HU (1) | HUP0003023A3 (fr) |
| IL (1) | IL133398A0 (fr) |
| IS (1) | IS5324A (fr) |
| MX (1) | MXPA99009120A (fr) |
| NO (1) | NO996496L (fr) |
| NZ (1) | NZ500212A (fr) |
| PL (1) | PL337665A1 (fr) |
| WO (1) | WO1999001417A1 (fr) |
| ZA (1) | ZA985668B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1110549A1 (fr) | 1999-12-23 | 2001-06-27 | Warner-Lambert Company | Utilisation de la trimébutine pour le traitemant de la douleur |
| 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 |
| FR2948660B1 (fr) | 2009-07-30 | 2011-08-19 | Oroxcell | Derives de 2-amino-2-phenyl-alkanol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| IN2014DN08379A (fr) * | 2012-03-12 | 2015-05-08 | Gicare Pharma Inc | |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1434826A (en) * | 1973-11-14 | 1976-05-05 | Gallardo Antonio Sa | Esters and carbamates of aminoalkanols |
-
1997
- 1997-06-30 FR FR9708323A patent/FR2765218B1/fr not_active Expired - Fee Related
-
1998
- 1998-06-23 NZ NZ500212A patent/NZ500212A/en unknown
- 1998-06-23 AU AU85405/98A patent/AU731887B2/en not_active Ceased
- 1998-06-23 IL IL13339898A patent/IL133398A0/xx unknown
- 1998-06-23 MX MXPA99009120A patent/MXPA99009120A/es unknown
- 1998-06-23 HU HU0003023A patent/HUP0003023A3/hu unknown
- 1998-06-23 WO PCT/EP1998/003825 patent/WO1999001417A1/fr not_active Ceased
- 1998-06-23 KR KR1019997012424A patent/KR20010014294A/ko not_active Ceased
- 1998-06-23 JP JP50625999A patent/JP2002508776A/ja active Pending
- 1998-06-23 EP EP98936382A patent/EP0993436A1/fr not_active Withdrawn
- 1998-06-23 BR BR9810387-3A patent/BR9810387A/pt not_active IP Right Cessation
- 1998-06-23 CA CA002285479A patent/CA2285479A1/fr not_active Abandoned
- 1998-06-23 PL PL98337665A patent/PL337665A1/xx unknown
- 1998-06-29 ZA ZA985668A patent/ZA985668B/xx unknown
-
1999
- 1999-12-27 NO NO996496A patent/NO996496L/no not_active Application Discontinuation
- 1999-12-28 IS IS5324A patent/IS5324A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002508776A (ja) | 2002-03-19 |
| AU731887B2 (en) | 2001-04-05 |
| HUP0003023A3 (en) | 2001-12-28 |
| CA2285479A1 (fr) | 1999-01-14 |
| FR2765218B1 (fr) | 1999-08-13 |
| IL133398A0 (en) | 2001-04-30 |
| EP0993436A1 (fr) | 2000-04-19 |
| WO1999001417A1 (fr) | 1999-01-14 |
| HUP0003023A2 (hu) | 2001-01-29 |
| PL337665A1 (en) | 2000-08-28 |
| AU8540598A (en) | 1999-01-25 |
| NZ500212A (en) | 2001-07-27 |
| ZA985668B (en) | 1999-01-25 |
| NO996496D0 (no) | 1999-12-27 |
| BR9810387A (pt) | 2000-09-05 |
| KR20010014294A (ko) | 2001-02-26 |
| NO996496L (no) | 1999-12-27 |
| IS5324A (is) | 1999-12-28 |
| FR2765218A1 (fr) | 1998-12-31 |
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