IL31265A - N - Phenylalkyl Phenylacitamides and 4, 3 - New dihydroisoquinolines - Google Patents
N - Phenylalkyl Phenylacitamides and 4, 3 - New dihydroisoquinolinesInfo
- Publication number
- IL31265A IL31265A IL31265A IL3126565A IL31265A IL 31265 A IL31265 A IL 31265A IL 31265 A IL31265 A IL 31265A IL 3126565 A IL3126565 A IL 3126565A IL 31265 A IL31265 A IL 31265A
- Authority
- IL
- Israel
- Prior art keywords
- designate
- designates
- hydrogen
- halogen
- group
- Prior art date
Links
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 methoxy, ethoxy Chemical group 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960004279 formaldehyde Drugs 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 150000002511 isochromanes Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BRLDZKPJJNASGG-KRWDZBQOSA-N alpha-berbine Chemical class C1=CC=C2CN3CCC4=CC=CC=C4[C@@H]3CC2=C1 BRLDZKPJJNASGG-KRWDZBQOSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR963667A FR1493408A (fr) | 1964-02-13 | 1964-02-13 | Nouveau procédé de préparation d'alcaloïdes tétracycliques dérivés de l'isoquinoléine et produits obtenus dans ce procédé |
| FR997A FR90553E (fr) | 1964-02-13 | 1965-01-06 | Nouveau procédé de préparation d'alcaloïdes tétracycliques dérivés de l'isoquinoléine et produits obtenus dans ce procédé |
| FR3343 | 1965-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL31265A true IL31265A (en) | 1969-11-12 |
Family
ID=27241841
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31265A IL31265A (en) | 1964-02-13 | 1965-02-08 | N - Phenylalkyl Phenylacitamides and 4, 3 - New dihydroisoquinolines |
| IL31264A IL31264A (en) | 1964-02-13 | 1965-02-08 | 12-halo-berbine derivatives |
| IL31263A IL31263A (en) | 1964-02-13 | 1965-02-08 | Isochromane compounds |
| IL22941A IL22941A (en) | 1964-02-13 | 1965-02-08 | A process for preparing the history of Rabin and certain new histories obtained in this process |
| IL31265A IL31265A0 (en) | 1964-02-13 | 1968-12-12 | Novel n-phenyl alkyl phenylacet amides |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31264A IL31264A (en) | 1964-02-13 | 1965-02-08 | 12-halo-berbine derivatives |
| IL31263A IL31263A (en) | 1964-02-13 | 1965-02-08 | Isochromane compounds |
| IL22941A IL22941A (en) | 1964-02-13 | 1965-02-08 | A process for preparing the history of Rabin and certain new histories obtained in this process |
| IL31265A IL31265A0 (en) | 1964-02-13 | 1968-12-12 | Novel n-phenyl alkyl phenylacet amides |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3426027A (cg-RX-API-DMAC10.html) |
| BR (1) | BR6567094D0 (cg-RX-API-DMAC10.html) |
| CH (2) | CH470393A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1620147B1 (cg-RX-API-DMAC10.html) |
| FR (3) | FR1493408A (cg-RX-API-DMAC10.html) |
| GB (3) | GB1095881A (cg-RX-API-DMAC10.html) |
| IL (5) | IL31265A (cg-RX-API-DMAC10.html) |
| NL (2) | NL6501747A (cg-RX-API-DMAC10.html) |
| SE (1) | SE306091B (cg-RX-API-DMAC10.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539642A (en) * | 1967-07-19 | 1970-11-10 | Geigy Chem Corp | 2-phenyl-2-(1-naphthyl)acetamides |
| US3755330A (en) * | 1967-08-25 | 1973-08-28 | Sandoz Ag | 1-{60 -hydroxybenzyl 3-methyl, 1,2,3,4-tetrahydroiso quinolino-2-carbonitriles |
| US4013666A (en) * | 1976-03-15 | 1977-03-22 | G. D. Searle & Co. | (8α,13Aβ)-8-CARBOCYCLIC/CARBOCYCLIC METHYL-5,8,13,13A-TETRAHYDRO-2,3,10,11-TETRAMETHOXY-6H-dibenzo[a,g]quinolizines and intermediates thereto |
| US4087426A (en) * | 1976-08-16 | 1978-05-02 | Research Corporation | Oxybisberberine and a process for its production |
| IE55519B1 (en) * | 1982-05-14 | 1990-10-10 | Maroko Peter R | Use of a protoberberine alkaloid and composition containing same |
| FR2537583B1 (fr) * | 1982-12-14 | 1985-08-09 | Urpha | Enantiomeres levogyres des derives de la tetrahydro-5, 6, 13, 13a 8h-dibenzo (a,g-) quinolizine, procedes d'obtention, compositions pharmaceutiques les contenant et application |
| CN102796096B (zh) * | 2011-05-27 | 2016-09-14 | 中国科学院上海药物研究所 | 六氢二苯并[a,g]喹嗪类化合物、其制备方法、药物组合物及其应用 |
| EP3670511A4 (en) | 2017-08-14 | 2020-09-02 | Shanghai Institute of Materia Medica, Chinese Academy of Sciences | TETRAHYDROPROTOBERBERINE COMPOUND, ITS PREPARATION PROCESS, ITS USES AND PHARMACEUTICAL COMPOSITION |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103513A (en) * | 1963-09-10 | Process for preparing hexadehy- | ||
| US2634292A (en) * | 1950-05-27 | 1953-04-07 | Hoffmann La Roche | Cyclohexenyl ethyl amine and process for the manufacture thereof |
| US2683713A (en) * | 1951-02-16 | 1954-07-13 | Lilly Co Eli | Substituted benzylisoquinolines |
| US3272707A (en) * | 1964-07-17 | 1966-09-13 | Smith Kline French Lab | Pharmaceutical compositions and methods for their use |
-
0
- NL NL129028D patent/NL129028C/xx active
-
1964
- 1964-02-13 FR FR963667A patent/FR1493408A/fr not_active Expired
-
1965
- 1965-01-06 FR FR997A patent/FR90553E/fr not_active Expired
- 1965-02-08 IL IL31265A patent/IL31265A/en unknown
- 1965-02-08 IL IL31264A patent/IL31264A/xx unknown
- 1965-02-08 IL IL31263A patent/IL31263A/xx unknown
- 1965-02-08 IL IL22941A patent/IL22941A/en unknown
- 1965-02-11 BR BR167094/65A patent/BR6567094D0/pt unknown
- 1965-02-11 CH CH638967A patent/CH470393A/fr not_active IP Right Cessation
- 1965-02-11 CH CH185265A patent/CH437330A/fr unknown
- 1965-02-12 GB GB6244/65A patent/GB1095881A/en not_active Expired
- 1965-02-12 GB GB15454/67A patent/GB1095882A/en not_active Expired
- 1965-02-12 GB GB15455/67A patent/GB1095883A/en not_active Expired
- 1965-02-12 US US432409A patent/US3426027A/en not_active Expired - Lifetime
- 1965-02-12 SE SE1885/65A patent/SE306091B/xx unknown
- 1965-02-12 NL NL6501747A patent/NL6501747A/xx unknown
- 1965-02-12 DE DE1965R0039899 patent/DE1620147B1/de not_active Withdrawn
- 1965-02-24 FR FR684465A patent/FR4771M/fr not_active Expired
-
1968
- 1968-12-12 IL IL31265A patent/IL31265A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1095883A (en) | 1967-12-20 |
| NL6501747A (cg-RX-API-DMAC10.html) | 1965-08-16 |
| IL31263A (en) | 1969-07-30 |
| FR90553E (fr) | 1968-01-05 |
| FR4771M (fr) | 1967-02-27 |
| IL22941A (en) | 1969-02-27 |
| SE306091B (cg-RX-API-DMAC10.html) | 1968-11-18 |
| IL31264A (en) | 1969-06-25 |
| US3426027A (en) | 1969-02-04 |
| IL31265A0 (en) | 1969-02-27 |
| GB1095882A (en) | 1967-12-20 |
| CH470393A (fr) | 1969-03-31 |
| DE1620147B1 (de) | 1972-05-31 |
| NL129028C (cg-RX-API-DMAC10.html) | |
| BR6567094D0 (pt) | 1973-12-26 |
| CH437330A (fr) | 1967-06-15 |
| GB1095881A (en) | 1967-12-20 |
| FR1493408A (fr) | 1967-09-01 |
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