CH637370A5 - Racemic forms and optically active forms of 2-(4-biphenylyl)-N-(diethylaminoalkyl)-propionamide, salts thereof and relative preparation processes - Google Patents
Racemic forms and optically active forms of 2-(4-biphenylyl)-N-(diethylaminoalkyl)-propionamide, salts thereof and relative preparation processes Download PDFInfo
- Publication number
- CH637370A5 CH637370A5 CH1216178A CH1216178A CH637370A5 CH 637370 A5 CH637370 A5 CH 637370A5 CH 1216178 A CH1216178 A CH 1216178A CH 1216178 A CH1216178 A CH 1216178A CH 637370 A5 CH637370 A5 CH 637370A5
- Authority
- CH
- Switzerland
- Prior art keywords
- propionamide
- bromide
- iodide
- compound according
- ethyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 13
- 229940080818 propionamide Drugs 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 23
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 16
- -1 3 - diethylaminopropyl propionamide Chemical compound 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 229940102396 methyl bromide Drugs 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 4
- MVFHRQWYCXYYMU-UHFFFAOYSA-N 3-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1C1=CC=CC=C1 MVFHRQWYCXYYMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims 6
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000812 cholinergic antagonist Substances 0.000 description 6
- 230000002445 parasympatholytic effect Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 3
- 229960004484 carbachol Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 206010039424 Salivary hypersecretion Diseases 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- JPKKQJKQTPNWTR-KQAYXBCTSA-N [(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2r)-3-hydroxy-2-phenylpropanoate;sulfuric acid;hydrate Chemical compound O.OS(O)(=O)=O.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1.C1([C@H](CO)C(=O)OC2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 JPKKQJKQTPNWTR-KQAYXBCTSA-N 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 2
- GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical compound [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 2
- 229960002777 dicycloverine Drugs 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 210000001087 myotubule Anatomy 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- CWAFBZDOGVLICK-UHFFFAOYSA-N propanamide;hydrobromide Chemical compound Br.CCC(O)=N CWAFBZDOGVLICK-UHFFFAOYSA-N 0.000 description 2
- 208000026451 salivation Diseases 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- JALUUBQFLPUJMY-UHFFFAOYSA-N 2-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 JALUUBQFLPUJMY-UHFFFAOYSA-N 0.000 description 1
- DWDRHYMGDMNKLL-UHFFFAOYSA-N 2-(4-phenylphenyl)propanoyl chloride Chemical compound C1(=CC=CC=C1)C1=CC=C(C=C1)C(C(=O)Cl)C DWDRHYMGDMNKLL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
- 101150046236 CNR1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- 241001415801 Sulidae Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- HOZOZZFCZRXYEK-GSWUYBTGSA-M butylscopolamine bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-GSWUYBTGSA-M 0.000 description 1
- 108010079344 calcyclin-associated protein 50 Proteins 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- BWNPPPLRJQXQCO-UHFFFAOYSA-N n',n'-bis(ethylamino)ethane-1,2-diamine Chemical compound CCNN(CCN)NCC BWNPPPLRJQXQCO-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- DTYCLCKCZXMPME-UHFFFAOYSA-N propanamide hydroiodide Chemical compound CCC(N)=O.I DTYCLCKCZXMPME-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 229950009846 scopolamine butylbromide Drugs 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 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 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT964377A IT1090782B (it) | 1977-11-30 | 1977-11-30 | 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH637370A5 true CH637370A5 (en) | 1983-07-29 |
Family
ID=11132874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1216178A CH637370A5 (en) | 1977-11-30 | 1978-11-28 | Racemic forms and optically active forms of 2-(4-biphenylyl)-N-(diethylaminoalkyl)-propionamide, salts thereof and relative preparation processes |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5490157A (OSRAM) |
| BE (1) | BE872403A (OSRAM) |
| CA (1) | CA1118446A (OSRAM) |
| CH (1) | CH637370A5 (OSRAM) |
| DE (1) | DE2851416A1 (OSRAM) |
| ES (1) | ES475533A1 (OSRAM) |
| FR (1) | FR2410641A1 (OSRAM) |
| IT (1) | IT1090782B (OSRAM) |
| NL (1) | NL7811698A (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20012025A1 (it) * | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| DK2049482T3 (en) * | 2006-08-08 | 2016-02-01 | Techfields Biochem Co Ltd | Positively charged, water-soluble prodrugs of aryl and heteroaryl acetic acids with very fast skin penetration rate |
| CN101506161B (zh) * | 2006-08-15 | 2013-11-13 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的水溶性的芳基和杂芳基丙酸类前药 |
| AU2013206218B2 (en) * | 2006-08-15 | 2016-06-30 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| EP2170826B1 (en) | 2007-06-04 | 2022-04-27 | Techfields Inc | Pro-drugs of nsaias with very high skin and membranes penetration rates and their new medicinal uses |
| KR20210123406A (ko) | 2008-12-04 | 2021-10-13 | 충시 위 | 고투과력을 가진 조성물 및 이의 적용 |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| JP6290947B2 (ja) * | 2016-02-05 | 2018-03-07 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1584547A (OSRAM) * | 1968-06-05 | 1969-12-26 | ||
| FR1593024A (OSRAM) * | 1968-09-18 | 1970-05-25 | ||
| FR2119846A1 (en) * | 1970-12-28 | 1972-08-11 | Choay Sa | N,n-diethylaminoethylamide of para isobutyl phenylacetic - acid - antiinflammatory and analgesic |
| US4145435A (en) * | 1976-11-12 | 1979-03-20 | The Upjohn Company | 2-aminocycloaliphatic amide compounds |
-
1977
- 1977-11-30 IT IT964377A patent/IT1090782B/it active
-
1978
- 1978-11-28 CH CH1216178A patent/CH637370A5/it not_active IP Right Cessation
- 1978-11-28 DE DE19782851416 patent/DE2851416A1/de active Granted
- 1978-11-29 ES ES475533A patent/ES475533A1/es not_active Expired
- 1978-11-29 NL NL7811698A patent/NL7811698A/xx not_active Application Discontinuation
- 1978-11-30 JP JP14730778A patent/JPS5490157A/ja active Granted
- 1978-11-30 BE BE192036A patent/BE872403A/xx not_active IP Right Cessation
- 1978-11-30 CA CA000317175A patent/CA1118446A/en not_active Expired
- 1978-11-30 FR FR7833889A patent/FR2410641A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1090782B (it) | 1985-06-26 |
| ES475533A1 (es) | 1980-01-16 |
| FR2410641A1 (fr) | 1979-06-29 |
| FR2410641B1 (OSRAM) | 1983-04-15 |
| NL7811698A (nl) | 1979-06-01 |
| BE872403A (fr) | 1979-03-16 |
| DE2851416A1 (de) | 1979-05-31 |
| JPS631286B2 (OSRAM) | 1988-01-12 |
| DE2851416C2 (OSRAM) | 1989-02-23 |
| CA1118446A (en) | 1982-02-16 |
| JPS5490157A (en) | 1979-07-17 |
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