DE2064879A1 - - Google Patents
Info
- Publication number
- DE2064879A1 DE2064879A1 DE19702064879 DE2064879A DE2064879A1 DE 2064879 A1 DE2064879 A1 DE 2064879A1 DE 19702064879 DE19702064879 DE 19702064879 DE 2064879 A DE2064879 A DE 2064879A DE 2064879 A1 DE2064879 A1 DE 2064879A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chloro
- general formula
- dibenzo
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GGGYQDMZPKVLLC-UHFFFAOYSA-N 3-chloro-2-methyl-n-phenylbenzamide Chemical compound CC1=C(Cl)C=CC=C1C(=O)NC1=CC=CC=C1 GGGYQDMZPKVLLC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 hydroxyalkoxyalkyl Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- FYDBWILNJORXCC-UHFFFAOYSA-N 4-chloro-2-methyl-N-phenylbenzamide Chemical compound ClC1=CC(=C(C(=O)NC2=CC=CC=C2)C=C1)C FYDBWILNJORXCC-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- YPYKUYQPXRBYQP-UHFFFAOYSA-N 5-chloro-2-methyl-n-phenylbenzamide Chemical compound CC1=CC=C(Cl)C=C1C(=O)NC1=CC=CC=C1 YPYKUYQPXRBYQP-UHFFFAOYSA-N 0.000 description 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 1
- MZNCVTCEYXDDIS-UHFFFAOYSA-N Mebenil Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=CC=C1 MZNCVTCEYXDDIS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N Methyl salicylate Natural products COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- CNIPMLJEWLMTCO-UHFFFAOYSA-N methyl 2-(3-chloro-2-methylanilino)benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=CC=CC(Cl)=C1C CNIPMLJEWLMTCO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYMPSOJKDIMXKZ-UHFFFAOYSA-N methyl n,n-diphenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OC)C1=CC=CC=C1 SYMPSOJKDIMXKZ-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- RHLIPLVNXYUJQV-UHFFFAOYSA-N n,n-diphenylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 RHLIPLVNXYUJQV-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6927226A FR2069831A1 (en, 2012) | 1969-08-07 | 1969-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2064879A1 true DE2064879A1 (en, 2012) | 1972-02-10 |
Family
ID=9038789
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702039396 Pending DE2039396A1 (de) | 1969-08-07 | 1970-08-07 | Neue Dibenzazepinderivate und ihre Herstellung |
| DE19702064879 Pending DE2064879A1 (en, 2012) | 1969-08-07 | 1970-08-07 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702039396 Pending DE2039396A1 (de) | 1969-08-07 | 1970-08-07 | Neue Dibenzazepinderivate und ihre Herstellung |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4939275B1 (en, 2012) |
| AT (2) | AT299211B (en, 2012) |
| BE (1) | BE754532A (en, 2012) |
| CH (1) | CH516560A (en, 2012) |
| CS (2) | CS163771B2 (en, 2012) |
| DE (2) | DE2039396A1 (en, 2012) |
| ES (2) | ES382564A1 (en, 2012) |
| FR (1) | FR2069831A1 (en, 2012) |
| GB (2) | GB1301366A (en, 2012) |
| IE (1) | IE34441B1 (en, 2012) |
| IL (1) | IL35070A0 (en, 2012) |
| LU (1) | LU61484A1 (en, 2012) |
| NL (1) | NL7011296A (en, 2012) |
| OA (1) | OA03651A (en, 2012) |
| PL (1) | PL82685B1 (en, 2012) |
| SU (2) | SU370777A3 (en, 2012) |
| ZA (1) | ZA705448B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198942B1 (en, 2012) * | 1972-09-12 | 1975-03-14 | Rhone Poulenc Ind | |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
| GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
-
0
- BE BE754532D patent/BE754532A/xx unknown
-
1969
- 1969-08-07 FR FR6927226A patent/FR2069831A1/fr not_active Withdrawn
-
1970
- 1970-07-29 OA OA53994A patent/OA03651A/xx unknown
- 1970-07-30 NL NL7011296A patent/NL7011296A/xx unknown
- 1970-08-03 SU SU1466527A patent/SU370777A3/ru active
- 1970-08-03 SU SU1663229A patent/SU399124A3/ru active
- 1970-08-04 CS CS5442A patent/CS163771B2/cs unknown
- 1970-08-04 CS CS7446*A patent/CS163772B2/cs unknown
- 1970-08-06 LU LU61484D patent/LU61484A1/xx unknown
- 1970-08-06 IE IE1014/70A patent/IE34441B1/xx unknown
- 1970-08-06 PL PL1970142553A patent/PL82685B1/pl unknown
- 1970-08-06 IL IL35070A patent/IL35070A0/xx unknown
- 1970-08-06 ZA ZA705448A patent/ZA705448B/xx unknown
- 1970-08-06 CH CH1186870A patent/CH516560A/fr not_active IP Right Cessation
- 1970-08-07 ES ES382564A patent/ES382564A1/es not_active Expired
- 1970-08-07 GB GB1301366D patent/GB1301366A/en not_active Expired
- 1970-08-07 AT AT721170A patent/AT299211B/de not_active IP Right Cessation
- 1970-08-07 GB GB1301367D patent/GB1301367A/en not_active Expired
- 1970-08-07 DE DE19702039396 patent/DE2039396A1/de active Pending
- 1970-08-07 AT AT581571A patent/AT301556B/de not_active IP Right Cessation
- 1970-08-07 DE DE19702064879 patent/DE2064879A1/de active Pending
- 1970-09-04 ES ES383390A patent/ES383390A1/es not_active Expired
-
1971
- 1971-04-13 JP JP46022821A patent/JPS4939275B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| LU61484A1 (en, 2012) | 1971-07-15 |
| SU370777A3 (en, 2012) | 1973-02-15 |
| BE754532A (fr) | 1971-02-08 |
| OA03651A (fr) | 1971-12-24 |
| FR2069831A1 (en, 2012) | 1971-09-10 |
| ZA705448B (en) | 1971-04-28 |
| SU399124A3 (en, 2012) | 1973-09-27 |
| CS163772B2 (en, 2012) | 1975-11-07 |
| ES382564A1 (es) | 1973-05-01 |
| CH516560A (fr) | 1971-12-15 |
| PL82685B1 (en) | 1975-10-31 |
| ES383390A1 (es) | 1973-02-16 |
| GB1301366A (en, 2012) | 1972-12-29 |
| CS163771B2 (en, 2012) | 1975-11-07 |
| AT301556B (de) | 1972-09-11 |
| IE34441L (en) | 1971-02-07 |
| IE34441B1 (en) | 1975-05-14 |
| NL7011296A (en, 2012) | 1971-02-09 |
| DE2039396A1 (de) | 1971-02-18 |
| AT299211B (de) | 1972-06-12 |
| JPS4939275B1 (en, 2012) | 1974-10-24 |
| GB1301367A (en, 2012) | 1972-12-29 |
| IL35070A0 (en) | 1970-10-30 |
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