NL8204626A - Nieuwe verbinding met analgetische, ontstekingsremmende en muco-regulerende activiteit, de bereiding daarvan en verwante farmaceutische verbindingen. - Google Patents
Nieuwe verbinding met analgetische, ontstekingsremmende en muco-regulerende activiteit, de bereiding daarvan en verwante farmaceutische verbindingen. Download PDFInfo
- Publication number
- NL8204626A NL8204626A NL8204626A NL8204626A NL8204626A NL 8204626 A NL8204626 A NL 8204626A NL 8204626 A NL8204626 A NL 8204626A NL 8204626 A NL8204626 A NL 8204626A NL 8204626 A NL8204626 A NL 8204626A
- Authority
- NL
- Netherlands
- Prior art keywords
- afp
- ibuprofen
- activity
- muco
- inflammative
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 title claims description 15
- 230000000202 analgesic effect Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 11
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound 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
- 230000001754 anti-pyretic effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- -1 2-hydroxy-3- (o-methoxyphenoxy) propyl Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000002221 antipyretic Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000370 acceptor Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 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 2
- XDEINICVRABBOL-UHFFFAOYSA-N 3-(2-methoxyphenoxy)propan-1-ol Chemical compound COC1=CC=CC=C1OCCCO XDEINICVRABBOL-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent 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 30
- 229960001680 ibuprofen Drugs 0.000 description 29
- 241001465754 Metazoa Species 0.000 description 16
- 241000700159 Rattus Species 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 210000000416 exudates and transudate Anatomy 0.000 description 5
- 210000000265 leukocyte Anatomy 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 239000003158 myorelaxant agent Substances 0.000 description 4
- 230000002685 pulmonary effect Effects 0.000 description 4
- 230000002040 relaxant effect Effects 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 230000010415 tropism Effects 0.000 description 4
- HCHGWJGULCROAK-UHFFFAOYSA-N 3-(2-methoxyphenoxy)propane-1,1-diol Chemical compound COC1=CC=CC=C1OCCC(O)O HCHGWJGULCROAK-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 206010020843 Hyperthermia Diseases 0.000 description 2
- 206010021118 Hypotonia 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
- 230000002349 favourable effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000036031 hyperthermia Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- TUZRJGVLAFMQEK-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1.CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 TUZRJGVLAFMQEK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102100022875 Hypoxia-inducible factor 1-alpha Human genes 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000002496 gastric effect Effects 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
- 208000015181 infectious disease Diseases 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000001569 mucosecretolytic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N p-menthan-3-ol Chemical compound CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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 |
|---|---|---|---|
| IT2007382 | 1982-03-10 | ||
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8204626A true NL8204626A (nl) | 1983-10-03 |
Family
ID=11163583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8204626A NL8204626A (nl) | 1982-03-10 | 1982-11-29 | Nieuwe verbinding met analgetische, ontstekingsremmende en muco-regulerende activiteit, de bereiding daarvan en verwante farmaceutische verbindingen. |
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) |
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| 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. |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
|---|---|
| JPH0121139B2 (enExample) | 1989-04-19 |
| 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 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |