CH505117A - Verfahren zur Herstellung einer psychotropen Verbindung - Google Patents
Verfahren zur Herstellung einer psychotropen VerbindungInfo
- Publication number
- CH505117A CH505117A CH324468A CH324468A CH505117A CH 505117 A CH505117 A CH 505117A CH 324468 A CH324468 A CH 324468A CH 324468 A CH324468 A CH 324468A CH 505117 A CH505117 A CH 505117A
- Authority
- CH
- Switzerland
- Prior art keywords
- product
- phenyl
- chloro
- methyl
- benzene
- Prior art date
Links
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229960002327 chloral hydrate Drugs 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 238000010521 absorption reaction Methods 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011872 intimate mixture Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 3
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 3
- 229960003965 antiepileptics Drugs 0.000 abstract description 3
- 239000003158 myorelaxant agent Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 239000000320 mechanical mixture Substances 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 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
- 229920002472 Starch Polymers 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62079967A | 1967-03-06 | 1967-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH505117A true CH505117A (de) | 1971-03-31 |
Family
ID=24487444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH324468A CH505117A (de) | 1967-03-06 | 1968-03-05 | Verfahren zur Herstellung einer psychotropen Verbindung |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT286991B (en]) |
| BE (1) | BE711676A (en]) |
| CH (1) | CH505117A (en]) |
| DK (1) | DK121234B (en]) |
| FI (1) | FI48351C (en]) |
| FR (2) | FR1583753A (en]) |
| GB (1) | GB1183060A (en]) |
| IE (1) | IE31974B1 (en]) |
| IL (1) | IL29580A (en]) |
| LU (1) | LU55619A1 (en]) |
| NL (2) | NL6803061A (en]) |
| NO (1) | NO119841B (en]) |
| SE (1) | SE342629B (en]) |
-
0
- NL NL138681D patent/NL138681C/xx active
-
1968
- 1968-03-05 CH CH324468A patent/CH505117A/de not_active IP Right Cessation
- 1968-03-05 IE IE25668A patent/IE31974B1/xx unknown
- 1968-03-05 NL NL6803061A patent/NL6803061A/xx unknown
- 1968-03-05 BE BE711676D patent/BE711676A/xx unknown
- 1968-03-05 SE SE289068A patent/SE342629B/xx unknown
- 1968-03-05 FR FR1583753D patent/FR1583753A/fr not_active Expired
- 1968-03-05 NO NO82568A patent/NO119841B/no unknown
- 1968-03-05 LU LU55619D patent/LU55619A1/xx unknown
- 1968-03-05 FI FI60168A patent/FI48351C/fi active
- 1968-03-05 IL IL2958068A patent/IL29580A/en unknown
- 1968-03-05 DK DK90368A patent/DK121234B/da unknown
- 1968-03-06 AT AT219668A patent/AT286991B/de not_active IP Right Cessation
- 1968-03-06 GB GB1099268A patent/GB1183060A/en not_active Expired
- 1968-06-05 FR FR153796A patent/FR7640M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1583753A (en]) | 1969-12-05 |
| NL6803061A (en]) | 1968-09-09 |
| IL29580A (en) | 1971-12-29 |
| NO119841B (en]) | 1970-07-13 |
| NL138681C (en]) | |
| GB1183060A (en) | 1970-03-04 |
| BE711676A (en]) | 1968-09-05 |
| IE31974L (en) | 1968-09-06 |
| FI48351B (en]) | 1974-05-31 |
| DE1670593A1 (de) | 1972-01-27 |
| LU55619A1 (en]) | 1969-10-02 |
| SE342629B (en]) | 1972-02-14 |
| DK121234B (da) | 1971-09-27 |
| FI48351C (fi) | 1974-09-10 |
| AT286991B (de) | 1971-01-11 |
| DE1670593B2 (de) | 1975-12-04 |
| IE31974B1 (en) | 1973-03-07 |
| FR7640M (en]) | 1970-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |