CA1086315A - Morphanthridine derivatives - Google Patents
Morphanthridine derivativesInfo
- Publication number
- CA1086315A CA1086315A CA290,464A CA290464A CA1086315A CA 1086315 A CA1086315 A CA 1086315A CA 290464 A CA290464 A CA 290464A CA 1086315 A CA1086315 A CA 1086315A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compounds
- compound
- phase
- indicated
- 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.)
- Expired
Links
- IDWNSAXOQLJYOF-UHFFFAOYSA-N 11h-benzo[c][1]benzazepine Chemical class C1=NC2=CC=CC=C2CC2=CC=CC=C21 IDWNSAXOQLJYOF-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000003176 neuroleptic agent Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 and concentrated Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229960005333 tetrabenazine 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
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
- C07D223/20—Dibenz [b, e] azepines; Hydrogenated dibenz [b, e] azepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1415776A CH624682A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-10 | 1976-11-10 | |
| CH14157/.76 | 1976-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086315A true CA1086315A (en) | 1980-09-23 |
Family
ID=4398460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA290,464A Expired CA1086315A (en) | 1976-11-10 | 1977-11-08 | Morphanthridine derivatives |
Country Status (26)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3402060A1 (de) * | 1984-01-21 | 1985-08-01 | Dr. Karl Thomae Gmbh, 7950 Biberach | Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB8607684D0 (en) * | 1986-03-27 | 1986-04-30 | Ici America Inc | Thiazepine compounds |
| CA2093646A1 (en) * | 1990-10-10 | 1992-04-11 | Jesse K. Wong | Bis-benzo cyclohepta piperidylidene, piperidine and piperazine compounds, compositions and methods of use |
| IT1258790B (it) * | 1992-01-17 | 1996-02-29 | Angelini Francesco Ist Ricerca | Alchil derivati del trazodone |
| TW268005B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1992-05-29 | 1996-01-11 | Lilly Industries Ltd | |
| MXPA05002884A (es) * | 2002-09-18 | 2005-06-22 | Fmc Corp | Derivados triciclicos insecticidas. |
| AU2004206931A1 (en) * | 2003-01-23 | 2004-08-05 | Acadia Pharmaceuticals Inc. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| ES2324713T3 (es) * | 2003-12-22 | 2009-08-13 | Acadia Pharmaceuticals Inc. | Analogos de diaril(a,d)ciclohepteno amino-sustituidos como agonistas muscarinicos y metodos de tratamiento de trastornos neuropsiquiatricos. |
| CA2560671A1 (en) * | 2004-04-01 | 2006-01-05 | Acadia Pharmaceuticals Inc. | Crystalline forms of n-desmethylclozapine |
| US20070105836A1 (en) * | 2005-10-31 | 2007-05-10 | Lars Pettersson | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL140242B (nl) * | 1963-03-01 | 1973-11-15 | Wander Ag Dr A | Werkwijze voor het bereiden van op de 11-plaats door een basische groep gesubstitueerde dibenz (b.f.)(1.4) oxazepinen. |
| US3389139A (en) * | 1963-06-14 | 1968-06-18 | Wander Ag Dr A | 6-homopiperazino and piperazinomorphanthridines |
| GB1006156A (en) * | 1963-06-14 | 1965-09-29 | Wander Ag Dr A | 6-basic substituted morphanthridines |
| US3539573A (en) * | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| CH601287A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-08-06 | 1978-07-14 | Sandoz Ag |
-
1976
- 1976-11-10 CH CH1415776A patent/CH624682A5/de not_active IP Right Cessation
-
1977
- 1977-11-01 FI FI773273A patent/FI64143C/fi not_active IP Right Cessation
- 1977-11-01 DK DK485677AA patent/DK140724B/da not_active IP Right Cessation
- 1977-11-02 SE SE7712387A patent/SE435510B/xx unknown
- 1977-11-02 DE DE2748920A patent/DE2748920C2/de not_active Expired
- 1977-11-04 GB GB45932/77A patent/GB1592329A/en not_active Expired
- 1977-11-04 GB GB16347/80A patent/GB1592330A/en not_active Expired
- 1977-11-04 NL NLAANVRAGE7712171,A patent/NL175297C/xx not_active IP Right Cessation
- 1977-11-04 CY CY1269A patent/CY1269A/xx unknown
- 1977-11-08 NZ NZ185642A patent/NZ185642A/xx unknown
- 1977-11-08 IL IL53332A patent/IL53332A/xx unknown
- 1977-11-08 NZ NZ191043A patent/NZ191043A/xx unknown
- 1977-11-08 PT PT67247A patent/PT67247B/pt unknown
- 1977-11-08 PH PH20407A patent/PH13515A/en unknown
- 1977-11-08 CA CA290,464A patent/CA1086315A/en not_active Expired
- 1977-11-08 JP JP52133151A patent/JPS5929076B2/ja not_active Expired
- 1977-11-08 AU AU30467/77A patent/AU517829B2/en not_active Expired
- 1977-11-08 ES ES463971A patent/ES463971A1/es not_active Expired
- 1977-11-08 BE BE182454A patent/BE860613A/xx not_active IP Right Cessation
- 1977-11-08 FR FR7733524A patent/FR2370745A1/fr active Granted
- 1977-11-08 IE IE2279/77A patent/IE46262B1/en unknown
- 1977-11-09 SU SU772539049A patent/SU686616A1/ru active
- 1977-11-09 AT AT0799177A patent/AT366682B/de active
-
1980
- 1980-01-11 US US06/111,459 patent/US4308207A/en not_active Expired - Lifetime
-
1982
- 1982-07-15 HK HK322/82A patent/HK32282A/xx unknown
-
1984
- 1984-09-20 SG SG665/84A patent/SG66584G/en unknown
- 1984-10-17 KE KE3472A patent/KE3472A/xx unknown
- 1984-12-30 MY MY56/84A patent/MY8400056A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1178584A (en) | 3,4-dihydro-5h-2,3-benzodiazepine derivatives and a process for the preparation thereof | |
| KR101221864B1 (ko) | 4-［［(7ｒ)-8-사이클로펜틸-7-에틸-5,6,7,8-테트라하이드로-5-메틸-6-옥소-2-프테리디닐］아미노］-3-메톡시-ｎ-(1-메틸-4-피페리디닐)벤즈아미드의 수화물 및 다형체, 이들의 제조방법, 및 약제로서의 이들의 용도 | |
| CA1086315A (en) | Morphanthridine derivatives | |
| US3335134A (en) | Certain 3, 4-dihydrofluoreno[1, 9a, 9-e, f]1, 4-diazepin-3(2h)-ones | |
| NZ199162A (en) | 8-(3-arylpropyl)-3-phenylnortropan-3-ols | |
| GB1581500A (en) | Pyridobenzodiazepines | |
| US4478750A (en) | 1-Phenyl-azepinoindoles | |
| US4888335A (en) | 3-alkoxy-2-aminopropyl heterocyclic amines and their use as cardiovascular agents | |
| IE44316B1 (en) | Indazole derivatives | |
| US4406900A (en) | Neuroleptic use of morphanthridines | |
| US4032640A (en) | 4H-Benzo[4,5]cyclohepta[1,2-b]thiophenes | |
| US4235921A (en) | Treating muscular spasms and convulsions with 3-azabicyclo[3.1.0]hexanes | |
| CA2130678C (en) | 2,3,4,5-tetrahydro-1h-3-benzazepines and pharmaceutically acceptable acid addition salts thereof | |
| US4160766A (en) | Amino containing benzazepines | |
| IE46381B1 (en) | 1,2,3,4,4a,10b-hexahydro-benz(f)isoquinolines | |
| US4010280A (en) | Phenoxyalkylamine derivatives and preparation thereof | |
| US3084161A (en) | New 3-methylsulphinyl phenothiazine derivatives | |
| US3635962A (en) | 4 - bis-morpholino- and 2 | |
| IE46263B1 (en) | A morphanthridine derivative | |
| US5856489A (en) | Process for the production of aminoazobicycloalkanes from oximes | |
| US4061752A (en) | 6-Piperazino-11-methylene-dibenzazepines[b,e] | |
| KR790001982B1 (ko) | 1, 2, 3, 4-테트라하이드로벤조 이소퀴놀린류의 제조방법 | |
| IE44449B1 (en) | 11-methylene-6-piperazinyl-morphanthridine derivatives | |
| US3634434A (en) | 3- or 4-dichloromethylene-piperidines | |
| US3882130A (en) | 4-Phenylethynyl benzylamines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |