JPH0121139B2 - - Google Patents
Info
- Publication number
- JPH0121139B2 JPH0121139B2 JP57210515A JP21051582A JPH0121139B2 JP H0121139 B2 JPH0121139 B2 JP H0121139B2 JP 57210515 A JP57210515 A JP 57210515A JP 21051582 A JP21051582 A JP 21051582A JP H0121139 B2 JPH0121139 B2 JP H0121139B2
- Authority
- JP
- Japan
- Prior art keywords
- ibuprofen
- formula
- isobutylphenyl
- methoxyphenoxy
- afp860
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 230000001754 anti-pyretic effect Effects 0.000 claims description 5
- 210000003097 mucus Anatomy 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- QXVRLFIKHYCFJS-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoyl chloride Chemical compound CC(C)CC1=CC=C(C(C)C(Cl)=O)C=C1 QXVRLFIKHYCFJS-UHFFFAOYSA-N 0.000 claims description 3
- HCHGWJGULCROAK-UHFFFAOYSA-N 3-(2-methoxyphenoxy)propane-1,1-diol Chemical compound COC1=CC=CC=C1OCCC(O)O HCHGWJGULCROAK-UHFFFAOYSA-N 0.000 claims description 3
- LXLBERKKIVYKNZ-UHFFFAOYSA-N [2-hydroxy-3-(2-methoxyphenoxy)propyl] 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound COC1=CC=CC=C1OCC(O)COC(=O)C(C)C1=CC=C(CC(C)C)C=C1 LXLBERKKIVYKNZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000002221 antipyretic Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- -1 2-hydroxy-3-(o-methoxyphenoxy)propyl 2-(p-isobutylphenyl)propionic acid Chemical compound 0.000 claims description 2
- 206010062530 Increased bronchial secretion Diseases 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 29
- 229960001680 ibuprofen Drugs 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 239000000679 carrageenan Substances 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 229940113118 carrageenan Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000002040 relaxant effect Effects 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 206010037660 Pyrexia Diseases 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 230000010415 tropism Effects 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 208000012895 Gastric disease Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 208000008423 pleurisy Diseases 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- APEODKDQAWQDLW-UHFFFAOYSA-N 2-hydroxy-2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)(O)C(O)=O)C=C1 APEODKDQAWQDLW-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 210000004224 pleura Anatomy 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20073/82A IT1190727B (it) | 1982-03-10 | 1982-03-10 | Composto ad attivita' analgesica,antiinfiammatoria e mucoregolatrice procedimento per la sua preparazione e relative composizioni farmaceutiche |
| IT20073A/82 | 1982-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58162554A JPS58162554A (ja) | 1983-09-27 |
| JPH0121139B2 true JPH0121139B2 (enExample) | 1989-04-19 |
Family
ID=11163583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57210515A Granted JPS58162554A (ja) | 1982-03-10 | 1982-11-29 | ２−（ｐ−イソブチルフエニル）プロピオン酸誘導体、その製造法およびそれを有効成分とする医薬 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4501914A (enExample) |
| JP (1) | JPS58162554A (enExample) |
| BE (1) | BE895111A (enExample) |
| CH (1) | CH650491A5 (enExample) |
| DE (1) | DE3242961C2 (enExample) |
| ES (1) | ES517685A0 (enExample) |
| FR (1) | FR2523124B1 (enExample) |
| GB (1) | GB2116541B (enExample) |
| GR (1) | GR77030B (enExample) |
| IT (1) | IT1190727B (enExample) |
| LU (1) | LU84486A1 (enExample) |
| NL (1) | NL8204626A (enExample) |
| PT (1) | PT75894B (enExample) |
| ZA (1) | ZA827898B (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1212840B (it) * | 1983-11-28 | 1989-11-30 | Zambeletti Spa L | Derivati di acidi bifenililalcanoici, loro preparazione e composizioni farmaceutiche che licontengono. |
| WO2014037832A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment of epilepsy and neurological diseases |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| JP2015519333A (ja) | 2012-05-07 | 2015-07-09 | セリックスビオ プライヴェート リミテッド | 神経疾患の治療のための組成物および方法 |
| CN104603096A (zh) | 2012-05-07 | 2015-05-06 | 塞利克斯比奥私人有限公司 | 用于治疗神经肌肉障碍和神经退行性疾病的组合物和方法 |
| WO2013168025A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of blood clotting disorders |
| US9266823B2 (en) | 2012-05-08 | 2016-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of parkinson's disease |
| WO2013167991A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic disorders |
| US20150133533A1 (en) * | 2012-05-08 | 2015-05-14 | Mahesh Kandula | Compositions and methods for the treatment of cough |
| WO2013167992A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of inflammatory disorders |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| US9346742B2 (en) | 2012-05-10 | 2016-05-24 | Cellix Bio Private Limited | Compositions and methods for the treatment of fibromyalgia pain |
| US9315478B2 (en) | 2012-05-10 | 2016-04-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9242939B2 (en) | 2012-05-10 | 2016-01-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| US9573927B2 (en) | 2012-05-10 | 2017-02-21 | Cellix Bio Private Limited | Compositions and methods for the treatment of severe pain |
| US9315461B2 (en) | 2012-05-10 | 2016-04-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| US9339484B2 (en) | 2012-05-10 | 2016-05-17 | Cellix Bio Private Limited | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| US9394288B2 (en) | 2012-05-10 | 2016-07-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of asthma and allergy |
| WO2013168033A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neurologic diseases |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| US9403857B2 (en) | 2012-05-10 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168011A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of chronic pain |
| WO2013168014A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| WO2013168001A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| JP6202287B2 (ja) | 2012-05-23 | 2017-09-27 | セリックスビオ プライヴェート リミテッド | 炎症性腸疾患の治療のための組成物及び方法 |
| EP2852571A4 (en) | 2012-05-23 | 2015-11-25 | Cellix Bio Private Ltd | COMPOSITIONS AND METHOD FOR THE TREATMENT OF MUCOSITIS |
| WO2013175344A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| WO2013175347A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| WO2013175376A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of local pain |
| JP2015518854A (ja) | 2012-05-23 | 2015-07-06 | セリックスビオ プライヴェート リミテッド | 多発性硬化症の治療のための組成物および方法 |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9187427B2 (en) | 2012-08-03 | 2015-11-17 | Cellix Bio Private Limited | N-substituted nicotinamide compounds and compositions for the treatment migraine and neurologic diseases |
| WO2014037833A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment inflammation and lipid disorders |
| US9670153B2 (en) | 2012-09-08 | 2017-06-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammation and lipid disorders |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| SG11201509782TA (en) | 2013-06-04 | 2015-12-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| NZ736131A (en) | 2014-09-26 | 2019-04-26 | Cellix Bio Private Ltd | Compositions and methods for the treatment of epilepsy and neurological disorders |
| JP6698643B2 (ja) | 2014-09-29 | 2020-05-27 | セリックス バイオ プライヴェート リミテッドＣｅｌｌｉｘ Ｂｉｏ Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 多発性硬化症の治療のための組成物及び方法 |
| EP3212626B1 (en) | 2014-10-27 | 2018-11-07 | Cellix Bio Private Limited | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| EP3242869B1 (en) | 2015-01-06 | 2021-10-27 | Cellixbio Private Limited | Compositions and methods for the treatment of inflammation and pain |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150137A (en) * | 1975-12-24 | 1979-04-17 | Hisamitsu Pharmaceutical Co. Inc. | Pyridylalkyl esters of 2-(p-isobutylphenyl)acetic acid and propionic acids and use |
| IT1064751B (it) * | 1976-07-09 | 1985-02-25 | Acraf | P. isobutil idratropato di guaiacolo |
-
1982
- 1982-03-10 IT IT20073/82A patent/IT1190727B/it active
- 1982-10-28 ZA ZA827898A patent/ZA827898B/xx unknown
- 1982-11-10 CH CH6536/82A patent/CH650491A5/it not_active IP Right Cessation
- 1982-11-12 US US06/441,106 patent/US4501914A/en not_active Expired - Fee Related
- 1982-11-20 DE DE3242961A patent/DE3242961C2/de not_active Expired
- 1982-11-23 GR GR69882A patent/GR77030B/el unknown
- 1982-11-24 BE BE2/59921A patent/BE895111A/nl not_active IP Right Cessation
- 1982-11-24 PT PT75894A patent/PT75894B/pt unknown
- 1982-11-24 LU LU84486A patent/LU84486A1/xx unknown
- 1982-11-24 FR FR8219679A patent/FR2523124B1/fr not_active Expired
- 1982-11-25 ES ES517685A patent/ES517685A0/es active Granted
- 1982-11-29 JP JP57210515A patent/JPS58162554A/ja active Granted
- 1982-11-29 GB GB08233933A patent/GB2116541B/en not_active Expired
- 1982-11-29 NL NL8204626A patent/NL8204626A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2523124A1 (fr) | 1983-09-16 |
| DE3242961C2 (de) | 1984-05-10 |
| ZA827898B (en) | 1983-08-31 |
| US4501914A (en) | 1985-02-26 |
| ES8401009A1 (es) | 1983-12-16 |
| DE3242961A1 (de) | 1983-09-15 |
| IT8220073A0 (it) | 1982-03-10 |
| LU84486A1 (fr) | 1983-06-13 |
| IT1190727B (it) | 1988-02-24 |
| GB2116541A (en) | 1983-09-28 |
| NL8204626A (nl) | 1983-10-03 |
| CH650491A5 (it) | 1985-07-31 |
| ES517685A0 (es) | 1983-12-16 |
| PT75894A (en) | 1982-12-01 |
| GB2116541B (en) | 1985-10-02 |
| JPS58162554A (ja) | 1983-09-27 |
| PT75894B (en) | 1986-01-15 |
| FR2523124B1 (fr) | 1985-07-19 |
| GR77030B (enExample) | 1984-09-04 |
| BE895111A (nl) | 1983-03-16 |
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