CA1043262A - Procede de preparation de nouvelles compositions pharmaceutiques renfermant un derive de la quinoleine - Google Patents
Procede de preparation de nouvelles compositions pharmaceutiques renfermant un derive de la quinoleineInfo
- Publication number
- CA1043262A CA1043262A CA226,516A CA226516A CA1043262A CA 1043262 A CA1043262 A CA 1043262A CA 226516 A CA226516 A CA 226516A CA 1043262 A CA1043262 A CA 1043262A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- phenyl
- pharmaceutical compositions
- hydrochloride
- compositions containing
- 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.)
- Expired
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical class C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 229960003403 betaine hydrochloride Drugs 0.000 claims abstract description 8
- 150000007513 acids Chemical class 0.000 claims abstract description 6
- WGUGHMBECREKMG-UHFFFAOYSA-N 8-(trifluoromethyl)quinolin-2-amine Chemical compound C1=CC=C(C(F)(F)F)C2=NC(N)=CC=C21 WGUGHMBECREKMG-UHFFFAOYSA-N 0.000 claims abstract description 4
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- APQPGQGAWABJLN-UHFFFAOYSA-N Floctafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 APQPGQGAWABJLN-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract description 4
- -1 o- (2 ', 3'-dihydroxypropyloxycarbonyl) phenyl Chemical group 0.000 abstract description 4
- 208000002193 Pain Diseases 0.000 abstract description 3
- 208000008035 Back Pain Diseases 0.000 abstract description 2
- 208000007514 Herpes zoster Diseases 0.000 abstract description 2
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 abstract description 2
- 208000008930 Low Back Pain Diseases 0.000 abstract description 2
- 208000019695 Migraine disease Diseases 0.000 abstract description 2
- 208000025747 Rheumatic disease Diseases 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 208000015181 infectious disease Diseases 0.000 abstract description 2
- 230000002458 infectious effect Effects 0.000 abstract description 2
- 229960005337 lysine hydrochloride Drugs 0.000 abstract description 2
- 210000003205 muscle Anatomy 0.000 abstract description 2
- 230000000552 rheumatic effect Effects 0.000 abstract description 2
- 208000006820 Arthralgia Diseases 0.000 abstract 1
- 208000000112 Myalgia Diseases 0.000 abstract 1
- 208000013465 muscle pain Diseases 0.000 abstract 1
- 208000004296 neuralgia Diseases 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- AJXUSUNIYLSPER-UHFFFAOYSA-N 8-(trifluoromethyl)quinoline Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1 AJXUSUNIYLSPER-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7416018A FR2269944B1 (enExample) | 1974-05-09 | 1974-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043262A true CA1043262A (fr) | 1978-11-28 |
Family
ID=9138625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,516A Expired CA1043262A (fr) | 1974-05-09 | 1975-05-08 | Procede de preparation de nouvelles compositions pharmaceutiques renfermant un derive de la quinoleine |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3988459A (enExample) |
| BE (1) | BE828818A (enExample) |
| CA (1) | CA1043262A (enExample) |
| DE (1) | DE2520818A1 (enExample) |
| DK (1) | DK200275A (enExample) |
| FR (1) | FR2269944B1 (enExample) |
| GB (1) | GB1507180A (enExample) |
| IE (1) | IE41053B1 (enExample) |
| NL (1) | NL7505459A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100779419B1 (ko) | 2005-07-26 | 2007-11-30 | 대한민국 | 중독성이 경감된 진통제 |
-
1974
- 1974-05-09 FR FR7416018A patent/FR2269944B1/fr not_active Expired
-
1975
- 1975-05-06 US US05/575,023 patent/US3988459A/en not_active Expired - Lifetime
- 1975-05-07 DK DK200275A patent/DK200275A/da unknown
- 1975-05-07 BE BE156134A patent/BE828818A/xx unknown
- 1975-05-08 CA CA226,516A patent/CA1043262A/fr not_active Expired
- 1975-05-08 GB GB19488/75A patent/GB1507180A/en not_active Expired
- 1975-05-09 IE IE1051/75A patent/IE41053B1/xx unknown
- 1975-05-09 NL NL7505459A patent/NL7505459A/xx not_active Application Discontinuation
- 1975-05-09 DE DE19752520818 patent/DE2520818A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IE41053B1 (en) | 1979-10-10 |
| DE2520818A1 (de) | 1975-11-20 |
| US3988459A (en) | 1976-10-26 |
| GB1507180A (en) | 1978-04-12 |
| FR2269944B1 (enExample) | 1978-02-03 |
| DK200275A (da) | 1975-11-10 |
| NL7505459A (nl) | 1975-11-11 |
| BE828818A (fr) | 1975-11-07 |
| IE41053L (en) | 1975-11-09 |
| FR2269944A1 (enExample) | 1975-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0098743B1 (en) | Phenyl alpha-acyloxyacetamide derivates and their therapeutic use | |
| JPH0144684B2 (enExample) | ||
| JPS61257951A (ja) | 新規なアリ−ル誘導体 | |
| JP2004518628A (ja) | 窒素含有化合物およびそれらのグリシン輸送阻害薬としての使用法 | |
| SA515360518B1 (ar) | مشتقات أمينو سيكلو بيوتان، وطريقة لتحضيرها، واستخدامها كعقاقير | |
| EP0068998B1 (fr) | Aryl-1 aminométhyl-2 cyclopropanes carboxylates (Z), leur préparation et leur application en tant que médicaments utiles dans le traitement d'algies diverses | |
| CA1043262A (fr) | Procede de preparation de nouvelles compositions pharmaceutiques renfermant un derive de la quinoleine | |
| WO2000067755A1 (en) | Cyclic amidines useful as nmda nr2b antagonists | |
| JPH05132430A (ja) | 薬物従属症及び禁断症状の治療に関するグリシン／ｎｍｄａレセプターリガンドの用法 | |
| US3944675A (en) | Substituted aryl and aralkyl amides in the treatment of parkinsonism | |
| FR2455590A1 (fr) | Nouveaux derives d'acide 2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)-benzoique, utiles notamment comme agents bloquants des recepteurs a- et b-adrenergiques, et leur procede de preparation | |
| TWI342210B (en) | 2-aminobenzoyl derivatives | |
| CA1091233A (fr) | Procede de preparation de nouveaux indoles substitues | |
| CA1128519A (fr) | Derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicaments | |
| EP0022017B1 (fr) | Nouveaux dérivés de benzoyl-2 nitro-4 anilides, leur préparation et leur application en tant que médicaments | |
| EP0001947A1 (fr) | Dérivés de l'amino-2 thiazoline, procédé de préparation et compositions pharmaceutiques les contenant | |
| JPS5892646A (ja) | ベンジリデン誘導体 | |
| US3993760A (en) | Pyrazinoisoquinolines as anthelmintic agents | |
| MC2105A1 (fr) | Derives de tetrahydronaphtalene | |
| EP0010030B1 (fr) | Nouveaux dérivés d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur préparation et leur application en tant que médicaments | |
| CA1263391A (fr) | N-carboxyalcoyl-2 oxo-3 diaryl 5-6 triazines utiles en therapeutique | |
| WO2007132280A1 (en) | Isatin and its derivatives for use as a medicament | |
| CA1223595A (fr) | Derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanamine et de (quinolyl-4)-1 (piperidyl-4)-3 propanamine, procedes pour leur preparation et medicaments les contenant | |
| TW200826923A (en) | A composition for the treatment and prevention of peptic ulcer | |
| EP0003200A2 (fr) | Dérivés du tétrahydro pyridinyl-indole et leurs sels, pour leur utilisation dans une méthode de traitement thérapeutique du corps humain ou animal, et compositions pharmaceutiques les renfermant |