PT99029A - Processo para a preparcao de derivados de benzazepina - Google Patents
Processo para a preparcao de derivados de benzazepina Download PDFInfo
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- PT99029A PT99029A PT99029A PT9902991A PT99029A PT 99029 A PT99029 A PT 99029A PT 99029 A PT99029 A PT 99029A PT 9902991 A PT9902991 A PT 9902991A PT 99029 A PT99029 A PT 99029A
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- Portugal
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- compound
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- alkyl
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- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 14
- 150000008038 benzoazepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 154
- 239000000203 mixture Substances 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 206010013663 drug dependence Diseases 0.000 claims description 7
- 208000011117 substance-related disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 230000036592 analgesia Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
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- 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
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- BXLHOSHUHPPGDV-UHFFFAOYSA-N 1h-azepin-2-ol Chemical compound OC1=CC=CC=CN1 BXLHOSHUHPPGDV-UHFFFAOYSA-N 0.000 description 7
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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- PEKXQMROUYTDAO-UHFFFAOYSA-N 3-(8-chloro-7-methoxy-3-methyl-4-oxo-2,5-dihydro-1h-3-benzazepin-5-yl)propanoic acid Chemical compound OC(=O)CCC1C(=O)N(C)CCC2=C1C=C(OC)C(Cl)=C2 PEKXQMROUYTDAO-UHFFFAOYSA-N 0.000 description 2
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- OULPWRUQLKSXBE-UHFFFAOYSA-N 11-methyl-11-azatricyclo[7.4.1.05,14]tetradeca-1(14),2,4-trien-4-ol Chemical compound C1N(C)CCC2=CC=C(O)C3=C2C1CCC3 OULPWRUQLKSXBE-UHFFFAOYSA-N 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
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- 235000005822 corn Nutrition 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
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- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 210000000944 nerve tissue Anatomy 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
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- 229940041678 oral spray Drugs 0.000 description 1
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- 239000006187 pill Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
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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
- C07D223/32—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems containing carbocyclic rings other than six-membered
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (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)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58789490A | 1990-09-25 | 1990-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT99029A true PT99029A (pt) | 1992-08-31 |
Family
ID=24351620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT99029A PT99029A (pt) | 1990-09-25 | 1991-09-24 | Processo para a preparcao de derivados de benzazepina |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5374722A (enExample) |
| EP (1) | EP0551312A1 (enExample) |
| JP (1) | JPH0615530B2 (enExample) |
| AU (1) | AU8536591A (enExample) |
| IE (1) | IE913343A1 (enExample) |
| IL (1) | IL99544A0 (enExample) |
| PT (1) | PT99029A (enExample) |
| TW (1) | TW238301B (enExample) |
| WO (1) | WO1992005157A1 (enExample) |
| ZA (1) | ZA917573B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6514964B1 (en) * | 1999-09-27 | 2003-02-04 | Amgen Inc. | Fused cycloheptane and fused azacycloheptane compounds and their methods of use |
| CN115427410B (zh) * | 2020-04-20 | 2024-02-23 | 苏州恩华生物医药科技有限公司 | 酰胺或者磺酰胺类衍生物及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769368A (en) * | 1986-02-10 | 1988-09-06 | Smithkline Beckman Corporation | 2,3,4,8,9,9A-Hexahydro-4-aryl-1H-indeno(1,7-CD)azepines |
| PH27337A (en) * | 1987-03-27 | 1993-06-08 | Schering Corp | Substituted benzazepines their preparation and pharmaceutical compositions containing them |
| US4957914A (en) * | 1987-05-15 | 1990-09-18 | Syntex (U.S.A.) Inc. | 1,9-alkano-bridged-2,3,4,5-tetrahydro-1H-3-benzazepines |
-
1991
- 1991-09-20 JP JP3515385A patent/JPH0615530B2/ja not_active Expired - Lifetime
- 1991-09-20 US US08/027,167 patent/US5374722A/en not_active Expired - Lifetime
- 1991-09-20 EP EP91916793A patent/EP0551312A1/en not_active Withdrawn
- 1991-09-20 AU AU85365/91A patent/AU8536591A/en not_active Abandoned
- 1991-09-20 WO PCT/US1991/006705 patent/WO1992005157A1/en not_active Ceased
- 1991-09-22 IL IL99544A patent/IL99544A0/xx unknown
- 1991-09-23 ZA ZA917573A patent/ZA917573B/xx unknown
- 1991-09-24 IE IE334391A patent/IE913343A1/en unknown
- 1991-09-24 TW TW080107524A patent/TW238301B/zh active
- 1991-09-24 PT PT99029A patent/PT99029A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992005157A1 (en) | 1992-04-02 |
| JPH05506246A (ja) | 1993-09-16 |
| IE913343A1 (en) | 1992-02-25 |
| JPH0615530B2 (ja) | 1994-03-02 |
| AU8536591A (en) | 1992-04-15 |
| IL99544A0 (en) | 1992-08-18 |
| TW238301B (enExample) | 1995-01-11 |
| ZA917573B (en) | 1992-06-24 |
| US5374722A (en) | 1994-12-20 |
| EP0551312A1 (en) | 1993-07-21 |
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Legal Events
| Date | Code | Title | Description |
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| BB1A | Laying open of patent application |
Effective date: 19920408 |
|
| FC3A | Refusal |
Effective date: 19981111 |