KR840003620A - 치환된 디벤조디아제피논의 제조방법 - Google Patents
치환된 디벤조디아제피논의 제조방법 Download PDFInfo
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- KR840003620A KR840003620A KR1019830000430A KR830000430A KR840003620A KR 840003620 A KR840003620 A KR 840003620A KR 1019830000430 A KR1019830000430 A KR 1019830000430A KR 830000430 A KR830000430 A KR 830000430A KR 840003620 A KR840003620 A KR 840003620A
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- methyl
- formula
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- pyridinyl
- acid
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 (1-methyl-4-piperidinyl)methyl Chemical group 0.000 claims abstract 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 10
- 239000002253 acid Substances 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 229910052801 chlorine Chemical group 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229910052744 lithium Inorganic materials 0.000 claims 3
- 150000007522 mineralic acids Chemical class 0.000 claims 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 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229940125810 compound 20 Drugs 0.000 claims 1
- 108010041382 compound 20 Proteins 0.000 claims 1
- WVPKAWVFTPWPDB-UHFFFAOYSA-N dichlorophosphinic acid Chemical compound OP(Cl)(Cl)=O WVPKAWVFTPWPDB-UHFFFAOYSA-N 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 239000012022 methylating agents Substances 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 208000006550 Mydriasis Diseases 0.000 abstract 1
- 230000001078 anti-cholinergic effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000028327 secretion Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- a)일반식(Ⅱ)의 디벤조디아제피논을 -25°내지 +130℃의 온도로 불활성용매중에서 일반식(Ⅲ)의 산유도체로 아실화하거나, 또는 b)R이 (1-메틸-1,2,5,6-테트라하이드로-4-피리디닐) 메틸 또는 1-메틸-1,2,5,6-테트라하이드로-4-피리디닐 그룹[이들 그룹은 임의로 헤테로-사이클릭환내에서 추가로 1개 또는 2개의 메틸그룹으로 치환된다]을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해서는, 일반식(Va)의 피리디늄염을 -40°내지 +50℃의 온도에서 양자성 용매중의 보로하이드라이드 또는 알콕시보로하이드라이드로 환원시키거나, 또는 c)R이 (1-메틸-1,2,5,6-테트라하이드로-4-피리디닐)-메틸, (1--메틸-1,2,5,6-테트라하이드로-4-피페리디닐리덴)메틸, (2,3-데하이드로-8-메틸-8-아자-비사이클로-[3,2,1]-옥트-3-일)-메틸 또는 (8-메틸-8-아자-비사이클로-[3,2,1]-옥트-3-일리덴) 메틸그룹[각 그룹들은 6원 헤테로 사이클릭환중에서 추가로 1개 또는 2개의 메틸그룹으로 임의 치환된다]을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해서는, 일반식(Ⅶ)의 5-디알킬포스포노아세틸-디벤조디아제피논을 20℃내지 반응혼합들의 비등점까지의 온도에서 용매중의 알칼리금속 하이드라이드 또는 알칼리금속 알콕사이드 존재하에 일반식(Ⅷ)의 피페리디논 또는 일반식(Ⅸ)의 트로피논과 반응시키거나, 또는 d)R이 (1-메틸-4-피페리디닐)-메틸 또는 엔도- 또는 엑소-(8-메틸-8-아자-비사이클로[3,2,1]-옥토-3-일)-메틸그룹[이들 그룹은 6원 헤케로-사이클릭환중에서 추가로 1개 또는 2개의 메틸그룹에 의해 임의로 치환된다]을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해서는, 일반식(Ⅹ)의 디벤조디아제피논을 촉매적으로 수소화시키거나, 또는 e)일반식(Ⅱ)의 디벤조디아제피논을 -60°내지 0℃의 온도, 유기용매중에서 적어도 2당량의 리튬 알킬, 리튬 아릴 또는 리튬 아마이드를 사용하여 그의 디-리튬염으로 전환시키고, 이어서 디-리튬염을 일반식(ⅩⅡ)의 에스테르와 반응시키며, 이어서 이렇게 하여 생성된 일반식(Ⅰ)의 화합물을 경우에 따라 무기 또는 유기산을 사용하여 그의 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ)의 치환된 디벤조디아제피논 및 그의 무기 또는 유기산과의 산부가염을 제조하는 방법.상기식에서, R1은 수소 또는 염소원자를 나타내고,R은 (1-메틸-4-피페리디닐)-메틸, (1-메틸-1,2,5,6-테트라하이드로-4-피리디닐)-메틸,1-메틸-1,2,5,6-테트라하이드로-4-피리디닐, (1-메틸-4-피페리디닐리덴)-메틸, (2,3-데하이드로-8-메틸-8-아자-비사이클로-[3,2,1]-옥토-3-일)-메틸, (8-메틸-8-아자-비사이클로-[3,2,1]-옥트-3-일리덴)메틸 또는 엔도-또는 엑소-(8-메틸-8-아자비사이클로-[3,2,1]-옥트-3-일)메틸그룹을 나타내며, 각 그룹은 헤케로사이클릭환 중에서 추가로 1개 또는 2개의 메틸그룹에 의해 임의 치환되고, Z는 소핵성 그룹을 나타내며, X는 강옥시산의 산그룹 또는 할로겐원자를 나타내고, RP는 추가로 1개 또는 2개의 매틸그룹에 의해 임의 치환된 4-피리디닐 또는 (4-피리디닐)-메틸그룹을 나타내며, R2는 탄소원자 1 내지 10의 알킬그룹을 나타내고, R3는 수소원자 또는 메킬그룹을 나타내며, R4는 다음과 같은 그룹을 나타내고,[여기에서, R3는 수소원자 또는 메틸그룹을 나타내며, X는 할로겐원자이다.] R5는 탄소원자 1 내지 10의 알킬그룹 또는 탄소원자 7 내지 13의 아르알킬 그룹을 나타낸다.
- 제1항의 a)에 있어서, 사용된 일반식(Ⅲ)의 산유도체가 산할라이드, 에스테르, 산무수물, 혼합 산무수물 또는 N-알킬-2-아실옥시피리디늄이며, 특히 강무기산(특히, 디클로로인산)과의 혼합 무수물이고, 반응을 임의로 산결합제 존재하의 불활성 용매 중에서 수행함을 특징으로 하는 방법.
- 제1항의 b)에 있어서, 일반식(Va)의 피리디늄염을양자성용매, 바람직하게는 물, 메탄올, 에탄올 또는 2-프로판올 또는 이들 용매의 혼합물 존재하에, -5° 내지 +10℃에서 나트륨 또는 칼륨 테트라하이드리도보레이트 또는 나트륨 또는 칼륨 알콕시-, 디알콕시- 또는 트리알콕시-브로하이드라이드를 사용하여 환원시킴을 특징으로 하는 방법.
- 일반식(Ⅱ)의 디벤조디아제피논을 반응혼합물의 비등점까지의 온도, 불활성 용매 중에서 일반식(Ⅳ)의 아실화제와 반응시켜 일반식(Ⅴ)의 화합물을 형성시키고, 이어서 생성된 화합물을 -20℃ 내지 +130℃, 불활성 용매중에서 일반식(Ⅵ)의 메틸화제로 메틸화하여 일반식(Va)의 상응하는 화합물을 형성시킴을 특징으로 하여, 일반식(Va)의 화합물을 제조하는 방법.상기식에서, R1은 수소 또는 염소원자를 나타내고, Z는 소핵성 그룹, 바람직하게는 염소, 브롬 또는 요오드원자를 나타내며, RP는 1개 또는 2개의 매틸그룹에 의해 임의 치환된 4-피리디닐 또는 (4-피리디닐)-메틸그룹을 나타내고, X는 강옥시산의 산그룹 또는 할로겐원자를 나타낸다.
- 제1항의 d)에 있어서, 수소화를 10 내지 40℃의 온도와 1 내지 50바아의 수소 압력하에서 플라티늄 디옥사이드 또는 목탄상 필라듐 또는 라니닉켈 또는 라니코발트를 사용하여 수행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3204157.8 | 1982-02-06 | ||
| DE19823204157 DE3204157A1 (de) | 1982-02-06 | 1982-02-06 | Substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
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| Publication Number | Publication Date |
|---|---|
| KR840003620A true KR840003620A (ko) | 1984-09-15 |
| KR900005278B1 KR900005278B1 (ko) | 1990-07-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830000430A KR900005278B1 (ko) | 1982-02-06 | 1983-02-04 | 치환된 디벤조디아제피논의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4447434A (ko) |
| EP (1) | EP0085892B1 (ko) |
| JP (1) | JPS58146581A (ko) |
| KR (1) | KR900005278B1 (ko) |
| AT (1) | ATE17002T1 (ko) |
| AU (1) | AU557463B2 (ko) |
| CA (1) | CA1189507A (ko) |
| CS (1) | CS241138B2 (ko) |
| DD (1) | DD207200A1 (ko) |
| DE (2) | DE3204157A1 (ko) |
| DK (1) | DK48983A (ko) |
| ES (5) | ES8403120A1 (ko) |
| FI (1) | FI75818C (ko) |
| GB (1) | GB2115411B (ko) |
| GR (1) | GR78060B (ko) |
| HK (1) | HK90189A (ko) |
| HU (1) | HU190708B (ko) |
| IE (1) | IE54552B1 (ko) |
| IL (1) | IL67836A (ko) |
| NO (1) | NO158623C (ko) |
| NZ (1) | NZ203192A (ko) |
| PL (1) | PL138523B1 (ko) |
| PT (1) | PT76198B (ko) |
| SU (1) | SU1301314A3 (ko) |
| ZA (1) | ZA83774B (ko) |
Families Citing this family (10)
| 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 |
| DE3531682A1 (de) * | 1985-09-05 | 1987-03-12 | Thomae Gmbh Dr K | (+)-6-chlor-5,10-dihydro-5-((1-methyl-4- piperidinyl)acetyl)-11h-dibenzo(b,e)(1,4) diazepin-11-on, seine isolierung und verwendung als arzneimittel |
| US4719149A (en) | 1986-02-28 | 1988-01-12 | Minnesota Mining And Manufacturing Company | Method for priming hard tissue |
| DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3738980A1 (de) * | 1987-11-17 | 1989-05-24 | Thomae Gmbh Dr K | Mittel zur behandlung von ischaemischen herzerkrankungen |
| DE3838912A1 (de) * | 1988-11-17 | 1990-05-23 | Thomae Gmbh Dr K | Mittel zur behandlung von akuten und chronischen obstruktiven atemwegserkrankungen |
| BRPI0006503B1 (pt) * | 2000-02-04 | 2017-05-09 | Biolab Sanus Farmacêutica Ltda | composição em forma de gel, creme, aerosol, spray, líquida e liofilizada de substância carreadora de produtos à base de papaína |
| CA2508956A1 (en) * | 2002-12-20 | 2004-07-15 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| WO2007056388A2 (en) * | 2005-11-07 | 2007-05-18 | The General Hospital Corporation | Compositions and methods for modulating poly (adp-ribose) polymerase activity |
| CN103980212A (zh) * | 2014-05-15 | 2014-08-13 | 南京工业大学 | 一锅法合成二苯二氮卓杂环衍生物的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795176C3 (de) * | 1968-08-20 | 1974-10-24 | Dr. Karl Thomae Gmbh, 7950 Biberach | hT-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung |
| IL61642A0 (en) * | 1979-12-20 | 1981-01-30 | Beecham Group Ltd | Aniline derivatives,their preparation and pharmalceutical compositions containing them |
| DE3028001A1 (de) * | 1980-07-24 | 1982-02-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
-
1982
- 1982-02-06 DE DE19823204157 patent/DE3204157A1/de not_active Withdrawn
-
1983
- 1983-01-26 EP EP83100677A patent/EP0085892B1/de not_active Expired
- 1983-01-26 DE DE8383100677T patent/DE3361504D1/de not_active Expired
- 1983-01-26 AT AT83100677T patent/ATE17002T1/de not_active IP Right Cessation
- 1983-01-31 US US06/462,149 patent/US4447434A/en not_active Expired - Fee Related
- 1983-02-01 FI FI830337A patent/FI75818C/fi not_active IP Right Cessation
- 1983-02-04 PT PT76198A patent/PT76198B/pt unknown
- 1983-02-04 NZ NZ203192A patent/NZ203192A/en unknown
- 1983-02-04 SU SU833550248A patent/SU1301314A3/ru active
- 1983-02-04 PL PL1983240437A patent/PL138523B1/pl unknown
- 1983-02-04 ZA ZA83774A patent/ZA83774B/xx unknown
- 1983-02-04 DK DK48983A patent/DK48983A/da not_active Application Discontinuation
- 1983-02-04 AU AU11123/83A patent/AU557463B2/en not_active Ceased
- 1983-02-04 KR KR1019830000430A patent/KR900005278B1/ko not_active IP Right Cessation
- 1983-02-04 IE IE219/83A patent/IE54552B1/en not_active IP Right Cessation
- 1983-02-04 IL IL67836A patent/IL67836A/xx unknown
- 1983-02-04 CA CA000420920A patent/CA1189507A/en not_active Expired
- 1983-02-04 JP JP58017291A patent/JPS58146581A/ja active Granted
- 1983-02-04 CS CS83784A patent/CS241138B2/cs unknown
- 1983-02-04 GB GB08303102A patent/GB2115411B/en not_active Expired
- 1983-02-04 ES ES519531A patent/ES8403120A1/es not_active Expired
- 1983-02-04 HU HU83396A patent/HU190708B/hu not_active IP Right Cessation
- 1983-02-04 GR GR70419A patent/GR78060B/el unknown
- 1983-02-04 NO NO830386A patent/NO158623C/no unknown
- 1983-02-04 DD DD83247724A patent/DD207200A1/xx not_active IP Right Cessation
- 1983-10-25 ES ES526727A patent/ES526727A0/es active Granted
- 1983-10-25 ES ES526728A patent/ES526728A0/es active Granted
- 1983-10-25 ES ES526729A patent/ES526729A0/es active Granted
- 1983-10-25 ES ES526726A patent/ES526726A0/es active Granted
-
1989
- 1989-11-16 HK HK901/89A patent/HK90189A/xx unknown
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