CH396931A - Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten - Google Patents
Verfahren zur Herstellung von basisch substituierten Diphenylalkan-DerivatenInfo
- Publication number
- CH396931A CH396931A CH463064A CH463064A CH396931A CH 396931 A CH396931 A CH 396931A CH 463064 A CH463064 A CH 463064A CH 463064 A CH463064 A CH 463064A CH 396931 A CH396931 A CH 396931A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- acid
- preparation
- basic
- diphenylalkane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003218 coronary vasodilator agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BNSBFWVSQWAIRE-UHFFFAOYSA-N N-(2-chloroethyl)-1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine Chemical compound COC=1C=C(C=CC1OC)CC(C)N(C)CCCl BNSBFWVSQWAIRE-UHFFFAOYSA-N 0.000 description 1
- FAQZKFBRUIJLMN-UHFFFAOYSA-N N-(2-chloroethyl)-1-(3-methoxyphenyl)-N-methylpropan-2-amine Chemical compound COC1=CC=CC(CC(C)N(C)CCCl)=C1 FAQZKFBRUIJLMN-UHFFFAOYSA-N 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
- RVQHIMMWJPQRJZ-UHFFFAOYSA-N N-benzyl-N-(2-chloroethyl)-1-(2-methoxyphenyl)propan-2-amine Chemical compound COC1=C(C=CC=C1)CC(C)N(CC1=CC=CC=C1)CCCl RVQHIMMWJPQRJZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 240000007711 Peperomia pellucida Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FDGWQBDPBWXMSG-UHFFFAOYSA-N n-(2-chloroethyl)-n-methyl-1-phenylpropan-2-amine Chemical compound ClCCN(C)C(C)CC1=CC=CC=C1 FDGWQBDPBWXMSG-UHFFFAOYSA-N 0.000 description 1
- VTGPOBOBADKXHQ-UHFFFAOYSA-N n-benzyl-n-(2-chloroethyl)-1-(4-methoxyphenyl)propan-2-amine Chemical compound C1=CC(OC)=CC=C1CC(C)N(CCCl)CC1=CC=CC=C1 VTGPOBOBADKXHQ-UHFFFAOYSA-N 0.000 description 1
- BQFDBRUUSLIJHQ-UHFFFAOYSA-N n-benzyl-n-(2-chloroethyl)-1-phenylpropan-2-amine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)CC1=CC=CC=C1 BQFDBRUUSLIJHQ-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25702A DE1111642B (de) | 1958-05-07 | 1958-05-07 | Verfahren zur Herstellung von basisch substituierten Diphenylmethan-Derivaten mit Herz- und Kreislaufwirksamkeit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH396931A true CH396931A (de) | 1965-08-15 |
Family
ID=7091732
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH463064A CH396931A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH462764A CH388332A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH462864A CH388333A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH7291559A CH385878A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH708765A CH397710A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH462964A CH388334A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH463164A CH388328A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH463264A CH388329A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH462764A CH388332A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH462864A CH388333A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH7291559A CH385878A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH708765A CH397710A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH462964A CH388334A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH463164A CH388328A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
| CH463264A CH388329A (de) | 1958-05-07 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Diphenylalkan-Derivaten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3152173A (enExample) |
| BE (1) | BE578515A (enExample) |
| CH (8) | CH396931A (enExample) |
| CY (1) | CY277A (enExample) |
| DE (1) | DE1111642B (enExample) |
| FR (1) | FR553M (enExample) |
| GB (1) | GB916644A (enExample) |
| MY (1) | MY6400049A (enExample) |
| NL (2) | NL238796A (enExample) |
| OA (1) | OA01363A (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3262977A (en) * | 1962-03-10 | 1966-07-26 | Chinoin Gyogyszer Es Vegyeszet | N-aralkyl-1, 1-diphenyl-propylamine derivatives |
| NL296693A (enExample) * | 1962-08-16 | |||
| DK111894A (enExample) | 1962-11-15 | |||
| FR95908E (fr) * | 1963-11-09 | 1972-01-31 | Degussa | Procédé de préparation de nouvelles aminocétones et des alcools secondaires correspondants. |
| DE1231704B (de) | 1963-12-19 | 1967-01-05 | Josef Klosa Dipl Chem Dr Rer N | Verfahren zur Herstellung neuer Diaryl-alkylaminoverbindungen mit heterocyclischen Ringen |
| US3457354A (en) * | 1965-09-21 | 1969-07-22 | Merck & Co Inc | Treatment of hypertension with 2-hydroxy (or amino) - 4,5 - dihydroxyphenethylamine derivatives |
| US3895057A (en) * | 1967-10-13 | 1975-07-15 | Dainippon Pharmaceutical Co | Aminoalkanols and their pharmaceutically acceptable acid-addition salts, and production thereof |
| US4329367A (en) * | 1974-08-05 | 1982-05-11 | Ciba-Geigy Corporation | 1-(Aralkoxyphenyl)-2-(bis-arylalkylamino)-alkanes |
| DE2902172C2 (de) * | 1979-01-20 | 1984-05-10 | UOP Inc., 60016 Des Plaines, Ill. | Verfahren zur Herstellung eines N,N'-Dialkylphenylendiamins |
| DE3278278D1 (en) * | 1982-04-23 | 1988-05-05 | Caola Kozmetikai | Novel cosmetic compositions containing prenylamine and a process for their preparation |
| ATE41655T1 (de) * | 1985-04-16 | 1989-04-15 | Hoffmann La Roche | Phenaethanolaminderivate. |
| US6982251B2 (en) * | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
| CZ20032039A3 (cs) * | 2001-01-26 | 2004-01-14 | Schering Corporation | Farmaceutický prostředek |
| CA2434436A1 (en) * | 2001-01-26 | 2002-08-01 | Teddy Kosoglou | Combinations of sterol absorption inhibitor(s) with cardiovascular agent(s) for the treatment of vascular conditions |
| AR035739A1 (es) * | 2001-01-26 | 2004-07-07 | Schering Corp | Composiciones farmaceuticas y combinaciones terapeuticas que comprenden secuestrante (s) de los acidos biliares y de inhibidor (es) de la absorcion de los esteroles y el uso de dichas composiciones para la manufactura de un medicamento para el tratamiento de indicaciones vasculares |
| US7071181B2 (en) * | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
| EP1353695A2 (en) * | 2001-01-26 | 2003-10-22 | Schering Corporation | Combinations of nicotinic acid and derivatives thereof and sterol absorption inhibitor(s) and treatments for vascular indications |
| BRPI0206641B8 (pt) * | 2001-01-26 | 2021-05-25 | Merck Sharp & Dohme | uso de um inibidor da absorção de esteróis |
| SK288217B6 (sk) * | 2001-01-26 | 2014-08-05 | Merck Sharp & Dohme Corp. | Zmes, terapeutická kombinácia, farmaceutický prostriedok a ich použitie |
| PT1392287E (pt) * | 2001-05-25 | 2007-02-28 | Schering Corp | Métodos para tratamento de doença de alzheimer e/ou regulação dos níveis de peptídeos β amilóide num sujeito |
| DE60216300T2 (de) * | 2001-09-21 | 2007-06-28 | Schering Corp. | Behandlung von xanthom mittels azetidinon-derivate als hemmer der sterol absorption |
| US20030119808A1 (en) * | 2001-09-21 | 2003-06-26 | Schering Corporation | Methods of treating or preventing cardiovascular conditions while preventing or minimizing muscular degeneration side effects |
| US7053080B2 (en) * | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
| SI1427409T1 (sl) * | 2001-09-21 | 2009-02-28 | Schering Corp | Postopki za zdravljenje ali preprečevanje vaskularnega vnetja z uporabo zaviralca(-ev) absorpcije sterola |
| US7056906B2 (en) * | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
| RS20050106A (sr) | 2002-08-19 | 2007-11-15 | Pfizer Products Inc., | Kombinovana terapija hiperproliferativnih bolesti |
| AU2003291719A1 (en) * | 2002-11-06 | 2004-06-03 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| ES2311806T3 (es) | 2003-03-07 | 2009-02-16 | Schering Corporation | Compuesto de azetidinona sustituidos, fornulaciones y usos de los mismos para el tratamiento de hipercolesterolemia. |
| US7459442B2 (en) | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| CA2517573C (en) * | 2003-03-07 | 2011-12-06 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| CN1756756A (zh) | 2003-03-07 | 2006-04-05 | 先灵公司 | 取代的2－吖丁啶酮化合物、其制剂及其治疗高胆甾醇血症的用途 |
| EP1680189A2 (en) * | 2003-11-05 | 2006-07-19 | Schering Corporation | Combinations of lipid modulating agents and substituted azetidinones and treatments for vascular conditions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2601323A (en) * | 1949-02-02 | 1952-06-24 | Upjohn Co | Process for preparing 4, 4-diphenyl-6-dimethylamino-heptanone-3 |
| US2681934A (en) * | 1950-01-06 | 1954-06-22 | Commercial Solvents Corp | Substituted diphenylalkylamines |
| US2797242A (en) * | 1953-08-11 | 1957-06-25 | Parke Davis & Co | Substituted alpha-benzylphenethylamines and methods for producing the same |
| US2738347A (en) * | 1954-12-13 | 1956-03-13 | Olin Mathieson | Penicillin salt of benzhydryl-phenethylamine |
| US2872374A (en) * | 1955-02-02 | 1959-02-03 | Nat Drug Co | Muscle-relaxing tranquilizer compositions |
| US2894033A (en) * | 1955-11-15 | 1959-07-07 | Nl Combinatie Chem Ind | Antispasmodic 1, 1-diphenyl-3-dialkylaminopropane, and its tertiary and quaternary salts |
| US2854379A (en) * | 1956-06-06 | 1958-09-30 | Miles Lab | Tranquilizing composition comprising 2-ethyl-cis-crotonylurea |
| DE1058063B (de) * | 1957-02-08 | 1959-05-27 | Hoechst Ag | Verfahren zur Herstellung von analgetisch wirksamen substituierten Phenylaethylaminen |
-
0
- BE BE578515D patent/BE578515A/xx unknown
- NL NL108640D patent/NL108640C/xx active
- NL NL238796D patent/NL238796A/xx unknown
-
1958
- 1958-05-07 DE DEF25702A patent/DE1111642B/de active Pending
-
1959
- 1959-05-05 CH CH463064A patent/CH396931A/de unknown
- 1959-05-05 CH CH462764A patent/CH388332A/de unknown
- 1959-05-05 CH CH462864A patent/CH388333A/de unknown
- 1959-05-05 CH CH7291559A patent/CH385878A/de unknown
- 1959-05-05 CH CH708765A patent/CH397710A/de unknown
- 1959-05-05 CH CH462964A patent/CH388334A/de unknown
- 1959-05-05 CH CH463164A patent/CH388328A/de unknown
- 1959-05-05 CH CH463264A patent/CH388329A/de unknown
- 1959-05-05 US US811011A patent/US3152173A/en not_active Expired - Lifetime
- 1959-05-07 GB GB15785/59A patent/GB916644A/en not_active Expired
-
1960
- 1960-08-31 FR FR837345A patent/FR553M/fr not_active Expired
-
1964
- 1964-02-12 CY CY27764A patent/CY277A/xx unknown
- 1964-12-31 MY MY196449A patent/MY6400049A/xx unknown
- 1964-12-31 OA OA51809A patent/OA01363A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH397710A (de) | 1965-08-31 |
| CH388334A (de) | 1965-02-28 |
| CH388332A (de) | 1965-02-28 |
| GB916644A (en) | 1963-01-23 |
| MY6400049A (en) | 1964-12-31 |
| DE1111642B (de) | 1961-07-27 |
| US3152173A (en) | 1964-10-06 |
| NL238796A (enExample) | |
| CH388333A (de) | 1965-02-28 |
| CY277A (en) | 1964-02-12 |
| FR553M (enExample) | 1961-05-29 |
| CH385878A (de) | 1964-12-31 |
| CH388329A (de) | 1965-02-28 |
| OA01363A (fr) | 1969-07-04 |
| NL108640C (enExample) | |
| CH388328A (de) | 1965-02-28 |
| BE578515A (enExample) |
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