KR840002838A - 피리도 [1,4] 벤조디아제핀 및 [2-[(니트로피리디닐) 아미노]페닐] 아릴메타논의 제조방법 - Google Patents
피리도 [1,4] 벤조디아제핀 및 [2-[(니트로피리디닐) 아미노]페닐] 아릴메타논의 제조방법 Download PDFInfo
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- KR840002838A KR840002838A KR1019820005903A KR820005903A KR840002838A KR 840002838 A KR840002838 A KR 840002838A KR 1019820005903 A KR1019820005903 A KR 1019820005903A KR 820005903 A KR820005903 A KR 820005903A KR 840002838 A KR840002838 A KR 840002838A
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- alk
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- -1 nitropyridinyl Chemical group 0.000 title claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims 3
- OPACCTXYZFTUOQ-UHFFFAOYSA-N 1h-pyrido[2,3-i][1,4]benzodiazepine Chemical class N1C=CN=CC2=CC=C(N=CC=C3)C3=C12 OPACCTXYZFTUOQ-UHFFFAOYSA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims 1
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 claims 1
- DCUWKDMFFUNGEH-UHFFFAOYSA-N CCCC(CC(=O)C1=CC=CC=C1)N(CCCN(C)C)C2=C(C=CC=N2)N Chemical compound CCCC(CC(=O)C1=CC=CC=C1)N(CCCN(C)C)C2=C(C=CC=N2)N DCUWKDMFFUNGEH-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- MRMOTKGMMJMALA-UHFFFAOYSA-N [2-[(3-nitropyridin-2-yl)amino]phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CN=C1NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MRMOTKGMMJMALA-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, ***e
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychiatry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Combination Of More Than One Step In Electrophotography (AREA)
- Paper (AREA)
- Luminescent Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 다음 일반식(Ⅳ)의 화합물을 일반식(Ⅲ)의 할로-니트로피리딘과 반응시켜 일반식(Ic)의 화합물을 제조하고, R이 수소인 생성물을 Q-alk1-할로화합물과 반응시켜 일반식(Ib)의 화합물을 제조하고, 일반식(Ic)의 (R=H,-CH3또는 C2H6-)화합물 또는 (R=-alk1-Q)화합물의 니트로그룹을 환원시켜 일반식(Ia)의 화합물을 제조하고, 이를 페환시켜 일반식(V)의 화합물을 제조하는 것을 특징으로 하여, 일반식(X)의 피리도[1,4]벤조디아제핀을 제조하는 방법.상기식에서, alk1은 1 내지 8을 함유하는 직쇄 또는 측쇄의 탄화수소쇄이며, Q는 수소, 할로겐 또는 -NR1R2그룹으로부터 선택되고, R1및 R2는 저급알킬, -C(O)-O- 저급알킬그룹으로 부터 선택되거나또는 인접한 질소원자와 함께 R1및 R2는 1-프탈리미도, 1-피롤리디닐, 1-피페리디닐, 4-모르폴리닐, 1-피페라지닐 및 4-치환된 -1-피페라지닐로 부터 선택된 선택된 해테로 사이클릭 잔기를 형성할 수 있으며, Ar은 2 혹은 3-티에닐, 2,3 또는4-피리미딜, 폐닐, 또는 할로,저급알킬,저급알콕시,트리플로로메틸 또는 니트로로 부터 선택된 같거나 다른1내지 3개의 기에 의해서 치환된 페닐그룹으로 부터 선택되고,Y는 수소 혹은 저급알킬,하이드록시,혹은 저급알콕시기로부터 선택된 같거나 다른1 내지 2개의 기로부터 선택되며, Z는수소,할로겐,저급알킬,하이드록시,저급알콕시 또는 니트로그룹으로부터 선택되고;단,일반식(Ⅳ)및 (Ic) R은 수소,메틸,또는 에틸그룹에서 선택되며;B는 카보닐,티옥소메틸,케탈 또는 티오케탈그룹에서 선택되고;일반식(Ib)에서R은 -alk1-Q [alk1및 Q는 상기 정의한 바와 같음)이고 일반식(Ia)에서 R은 수소 또는 -alk1-Q [alk1은 상기에 정의된 바와 같음)로 부터 선택된다.
- 2-클로로-3-니트로피리딘을 2-아미노-벤조페논과 반응시켜 [2-[(3-니트로-2-피리디닐)아미노]페닐]페닐메타논을 생성시키고, 상기 생성물을 3-디메틸아미노 프로필클로라이드와 반응시켜 [2-[[3-(디메틸아미노)프로필](3-니트로-2-피리디닐)아미노]페닐]페널메타논을 제조하고, 수득된 생성물을 염기성 조건하에서 환원시켜 [2-[[3-(디메틸아미노)프로필](3-아미노-2-피리디닐)아미노]폐닐]페닐메타논을 제조하고, 이를 산성 조건하에서 폐환시킴을 특징으로 하여 N,N-디메틸-6-페닐-11H-피리도[2,3-b][1,4]벤조디아제핀-11-프로판아민을 제조하는 방법.
- 다음 일반식(Ⅳ)의 화합물을 일반식(Ⅲ)의 할로-니트로피리딘과 반응시켜 일반식(Ic)의 화합물을 생성시키고, R이 수소인 일반식(Ic)의 화합물을 일반식 Q-alk1-할로의 화합물과 반응시켜 일반식(Ib)의 화합물을 생성시키고, 일반식(Ib)의 화합물의 니트로그룹을 아미노 그룹으로 환원시킴을 특징으로하여, 일반식(Ⅱ)의 [2-[(아미노피리디닐)아미노]페닐]아릴메타논 및 그 유도체를 제조하는 방법.여기에서 R은 수소 또는 -alk1-Q에서 선택되며; Q는 수소,-NR1R2또는 할로겐그룹중에서 선택되고; R1및 R2는 저급알킬 , -C(O)-O- 저급알킬그룹으로 부터 선택되거나 , 또는 인접한 질소원자와함께 R1및 R2는 1-피롤리디닐, 1-피페리디닐, 4-볼폴리닐, 1-피페라지닐 및 4-치환된 -1-피페라지닐로부터 선택된 헤페로사이클릭잔기를 형성할 수 있고; -alk1은 탄소원자 1내지 8을 함유하는 직쇄 또는 측쇄탄화수소이고; B는 카보닐, 티옥소메틸, 케탈 또는 티오케탈그룹으로부터 선택되고; Ar은 2 또는 3-티에닐,2,3 또는 4-피리디닐, 페닐 또는 할로, 저급알킬, 저급알콕시, 트리풀로로메틸 또는 니트로로부터 선택된 같거나 다른 1내지 3개의 기에 의해서 치환된 페닐그룹으로부터 선택되며; Y는 수소 또는 저급알킬, 하이드록시, 또는 저급알콕시기로부터 선택된 같거나 다른 1내지 2개의기로부터 선택되고; Z은 수소, 할로겐, 저급알킬, 하이드록시, 저급알콕시 또는 니트로그룹으로부터 선택되며 단, 일반식(Ⅳ)및 (Ic)에서 R은 수소, 메틸 또는 에틸그룹으로부터 선택되고,B는 카보닐, 티오닐, 케탈 또는 티오케탈로부터 선택되고 일반식(Ib)에서 R는 -alk1-Q( -alk1및 Q는 상기에 정의된바와 같음)이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US431997 | 1982-09-30 | ||
| US06/431,997 US4480100A (en) | 1982-09-30 | 1982-09-30 | [2-[(Nitropyridinyl)amino]phenyl]arymethanones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002838A true KR840002838A (ko) | 1984-07-21 |
| KR870000279B1 KR870000279B1 (ko) | 1987-02-23 |
Family
ID=23714311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205903A KR870000279B1 (ko) | 1982-09-30 | 1982-12-31 | 피리도 [1,4] 벤조디아제핀 및 [2-[(니트로피리디닐) 아미노]페닐] 아릴메타논의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4480100A (ko) |
| EP (1) | EP0107261B1 (ko) |
| JP (1) | JPS5970669A (ko) |
| KR (1) | KR870000279B1 (ko) |
| AT (1) | ATE37359T1 (ko) |
| AU (1) | AU550964B2 (ko) |
| CA (1) | CA1194869A (ko) |
| DE (1) | DE3378047D1 (ko) |
| DK (1) | DK547682A (ko) |
| EG (1) | EG16124A (ko) |
| ES (2) | ES518377A0 (ko) |
| FI (1) | FI77032C (ko) |
| GR (1) | GR77821B (ko) |
| HU (2) | HU190448B (ko) |
| IE (1) | IE54331B1 (ko) |
| IL (1) | IL67499A (ko) |
| IN (1) | IN156482B (ko) |
| NO (1) | NO160366C (ko) |
| NZ (1) | NZ202799A (ko) |
| PH (1) | PH20696A (ko) |
| PL (2) | PL145081B1 (ko) |
| PT (1) | PT76094B (ko) |
| YU (1) | YU125083A (ko) |
| ZA (1) | ZA829154B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4668675A (en) * | 1981-09-24 | 1987-05-26 | A. H. Robins Company, Incorporated | 2-[(amino-pyridinyl)amine]phenyl]aryl methanones, their thioxomethyl, ketal or thioketal analogs |
| US4560510A (en) * | 1984-04-06 | 1985-12-24 | A. H. Robins Company, Incorporated | Process and intermediates for the preparation of aryl substituted pyrido[1,4]benzodiazepines |
| US4628100A (en) * | 1984-04-06 | 1986-12-09 | A. H. Robins Company, Incorporated | Intermediates for the preparation of aryl substituted pyrido[1,4]benzodiazepines |
| US4749788A (en) * | 1987-04-13 | 1988-06-07 | A. H. Robins Company, Incorporated | Process for the preparation of aryl-pyrido(1,4) benzodiazepines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT327200B (de) * | 1972-09-06 | 1976-01-26 | Degussa | Verfahren zur herstellung von neuen aza-10,11-dihydro-5h-dibenzo (b,e)-(1,4) diazepinen sowie deren salzen |
| SE7605398L (sv) * | 1975-05-28 | 1976-11-29 | Merck & Co Inc | 3h-1,2,3-trizol(4,5-b)pyridiner |
-
1982
- 1982-09-30 US US06/431,997 patent/US4480100A/en not_active Expired - Lifetime
- 1982-12-07 NO NO824116A patent/NO160366C/no unknown
- 1982-12-09 DK DK547682A patent/DK547682A/da not_active Application Discontinuation
- 1982-12-10 FI FI824248A patent/FI77032C/fi not_active IP Right Cessation
- 1982-12-13 ZA ZA829154A patent/ZA829154B/xx unknown
- 1982-12-14 IN IN1443/CAL/82A patent/IN156482B/en unknown
- 1982-12-14 NZ NZ202799A patent/NZ202799A/en unknown
- 1982-12-14 PH PH28277A patent/PH20696A/en unknown
- 1982-12-16 IL IL67499A patent/IL67499A/xx unknown
- 1982-12-17 IE IE3009/82A patent/IE54331B1/en unknown
- 1982-12-20 ES ES518377A patent/ES518377A0/es active Granted
- 1982-12-22 AU AU91779/82A patent/AU550964B2/en not_active Ceased
- 1982-12-29 GR GR70180A patent/GR77821B/el unknown
- 1982-12-31 KR KR8205903A patent/KR870000279B1/ko active
-
1983
- 1983-01-07 DE DE8383300097T patent/DE3378047D1/de not_active Expired
- 1983-01-07 EP EP83300097A patent/EP0107261B1/en not_active Expired
- 1983-01-07 AT AT83300097T patent/ATE37359T1/de not_active IP Right Cessation
- 1983-01-14 PT PT76094A patent/PT76094B/pt unknown
- 1983-01-15 EG EG28/83A patent/EG16124A/xx active
- 1983-02-08 JP JP58019545A patent/JPS5970669A/ja active Pending
- 1983-05-12 HU HU831646A patent/HU190448B/hu not_active IP Right Cessation
- 1983-05-12 HU HU86500A patent/HU193360B/hu not_active IP Right Cessation
- 1983-05-13 PL PL1983252857A patent/PL145081B1/pl unknown
- 1983-05-13 PL PL1983241970A patent/PL139382B1/pl unknown
- 1983-05-30 CA CA000429140A patent/CA1194869A/en not_active Expired
- 1983-06-06 YU YU01250/83A patent/YU125083A/xx unknown
- 1983-08-11 ES ES524877A patent/ES524877A0/es active Granted
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