IL24802A - Divenzo-Cyclodheptins, their manufacture, and pharmaceutical preparations containing them - Google Patents
Divenzo-Cyclodheptins, their manufacture, and pharmaceutical preparations containing themInfo
- Publication number
- IL24802A IL24802A IL2480265A IL2480265A IL24802A IL 24802 A IL24802 A IL 24802A IL 2480265 A IL2480265 A IL 2480265A IL 2480265 A IL2480265 A IL 2480265A IL 24802 A IL24802 A IL 24802A
- Authority
- IL
- Israel
- Prior art keywords
- group
- product
- cycloheptene
- lower lower
- formulae
- Prior art date
Links
- 150000008508 dibenzocycloheptenes Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- -1 alkyl sulf Chemical compound 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 241000282320 Panthera leo Species 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- AJNHFFSGAYERKM-UHFFFAOYSA-N cycloheptene Chemical compound C1=CCCCCC1.C1=CCCCCC1 AJNHFFSGAYERKM-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RLLITDUMPMYNAJ-UHFFFAOYSA-N C1=CCCCCC1.C1=CC=CC=C1 Chemical compound C1=CCCCCC1.C1=CC=CC=C1 RLLITDUMPMYNAJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27B—SAWS FOR WOOD OR SIMILAR MATERIAL; COMPONENTS OR ACCESSORIES THEREFOR
- B27B33/00—Sawing tools for saw mills, sawing machines, or sawing devices
- B27B33/02—Structural design of saw blades or saw teeth
- B27B33/10—Hand saw blades
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23D—PLANING; SLOTTING; SHEARING; BROACHING; SAWING; FILING; SCRAPING; LIKE OPERATIONS FOR WORKING METAL BY REMOVING MATERIAL, NOT OTHERWISE PROVIDED FOR
- B23D61/00—Tools for sawing machines or sawing devices; Clamping devices for these tools
- B23D61/12—Straight saw blades; Strap saw blades
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42248864A | 1964-12-31 | 1964-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24802A true IL24802A (en) | 1969-05-28 |
Family
ID=23675113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2480265A IL24802A (en) | 1964-12-31 | 1965-12-15 | Divenzo-Cyclodheptins, their manufacture, and pharmaceutical preparations containing them |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL161432C (nl) * | 1968-01-30 | 1980-02-15 | Merck & Co Inc | Werkwijze ter bereiding van farmaceutische preparaten, de door toepassing daarvan verkregen gevormde farma- ceutische preparaten en werkwijze ter bereiding van polyhydrodibenzoa,d-cycloalkeenderivaten. |
| JPS54115360U (enrdf_load_stackoverflow) * | 1978-01-31 | 1979-08-13 |
-
1965
- 1965-12-15 IL IL2480265A patent/IL24802A/en unknown
- 1965-12-16 CH CH1735765A patent/CH492671A/de not_active IP Right Cessation
- 1965-12-16 FR FR42552A patent/FR1481056A/fr not_active Expired
- 1965-12-16 CH CH1170768A patent/CH461477A/de unknown
- 1965-12-16 NO NO16093065A patent/NO119796B/no unknown
- 1965-12-21 BR BR17586865A patent/BR6575868D0/pt unknown
- 1965-12-21 GB GB5401565A patent/GB1115327A/en not_active Expired
- 1965-12-21 GB GB3179567A patent/GB1115329A/en not_active Expired
- 1965-12-22 ES ES0321390A patent/ES321390A1/es not_active Expired
- 1965-12-22 DK DK656765A patent/DK134010B/da unknown
- 1965-12-29 BE BE674493D patent/BE674493A/xx unknown
- 1965-12-30 DE DE19651793549 patent/DE1793549A1/de active Pending
- 1965-12-30 DE DE19651543261 patent/DE1543261A1/de active Pending
- 1965-12-30 SE SE1698265A patent/SE322771B/xx unknown
- 1965-12-30 SE SE974167A patent/SE347739B/xx unknown
- 1965-12-31 NL NL6517264A patent/NL148587B/xx unknown
-
1966
- 1966-03-15 FR FR53549A patent/FR5669M/fr not_active Expired
-
1974
- 1974-11-11 JP JP12906974A patent/JPS518947B1/ja active Pending
- 1974-11-11 JP JP12907074A patent/JPS518948B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE322771B (enrdf_load_stackoverflow) | 1970-04-20 |
| GB1115329A (en) | 1968-05-29 |
| NL148587B (nl) | 1976-02-16 |
| DK134010C (enrdf_load_stackoverflow) | 1977-02-07 |
| SE347739B (enrdf_load_stackoverflow) | 1972-08-14 |
| NO119796B (enrdf_load_stackoverflow) | 1970-07-06 |
| DE1543261A1 (de) | 1969-09-11 |
| DK134010B (da) | 1976-08-30 |
| DE1793549A1 (de) | 1972-03-02 |
| NL6517264A (enrdf_load_stackoverflow) | 1966-07-04 |
| BR6575868D0 (pt) | 1973-09-06 |
| FR1481056A (fr) | 1967-05-19 |
| JPS518948B1 (enrdf_load_stackoverflow) | 1976-03-22 |
| BE674493A (enrdf_load_stackoverflow) | 1966-06-29 |
| JPS518947B1 (enrdf_load_stackoverflow) | 1976-03-22 |
| CH492671A (de) | 1970-06-30 |
| CH461477A (de) | 1968-08-31 |
| ES321390A1 (es) | 1966-06-16 |
| GB1115327A (en) | 1968-05-29 |
| FR5669M (enrdf_load_stackoverflow) | 1968-01-02 |
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