KR830007647A - 벤조헤테로사이클릭 화합물의 제조방법 - Google Patents
벤조헤테로사이클릭 화합물의 제조방법 Download PDFInfo
- Publication number
- KR830007647A KR830007647A KR1019810004999A KR810004999A KR830007647A KR 830007647 A KR830007647 A KR 830007647A KR 1019810004999 A KR1019810004999 A KR 1019810004999A KR 810004999 A KR810004999 A KR 810004999A KR 830007647 A KR830007647 A KR 830007647A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- process according
- carried out
- ring closure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 24
- 150000001875 compounds Chemical class 0.000 title claims 17
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 8
- 230000002378 acidificating effect Effects 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 150000007514 bases Chemical group 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- -1 quinoline compound Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- 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
- C07D471/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (23)
- 다음 일반식(Ⅱ)의 벤조헤테로사이클릭화합물을 폐환시키거나, 다음 일반식(Ⅲ)의 퀴놀린 화합물을 폐환시킨 후, 이 화합물을 가수분해시켜서 다음 일반식(Ⅰ)의 벤조헤테로사이클릭 화합물을 제조하는 방법.상기 일반식을 설명하면R1은 수소원자 또는 저급알킬기이며R2는 수소원자, 할로겐원자 또는 하이드록시기로 치환될 수 있는 저급알킬기이거나, 할로겐원자로 치환될 수 있는 저급알카노일기이며R3및 R4는 같거나 다르며, 이들 각각은 저급알킬기이며(단, n 이 1일 경우 R2는 할로겐원자로 치환된 저급알킬기가 아니어야 한다).R5는 상기 일반식(Ⅳ)의 벤조헤테로사이클릭화합물을 형성시킬 수 있는 저급알킬기이며X는 수소원자 또는 할로겐원자이며n은 1 또는 2이다(단, n이 1일 경우, R2는 할로겐원자로 치환된 저급알킬기가 아니어야 한다).
- 제1항에 있어서, 용매중에 일반식(Ⅱ) 또는 (Ⅲ)의 화합물을 약 100 내지 250℃온도로 가열시켜 폐환을 수행하는 상기 방법.
- 제2항에 있어서, 반응을 150 내지 200℃에서 수행하는 상기 방법.
- 제2항 또는 제3항에 있어서, 용매가 고비점 탄화수소 또는 고비점 에테르인 상기 방법.
- 제4항에 있어서, 용매가 테트라린, 디페닐에테르 또는 디에틸렌 글리콜 디메틸에테르인 상기 방법.
- 제1항에 있어서, 일반식(Ⅱ) 또는 (Ⅲ)화합물을 몰당 적어도 1몰의 과량의 산성 지지물을 사용하여 폐환을 약 100 내지 150℃에서 약 0.5 내지 6시간 동안 수행하는 상기 방법.
- 제6항에 있어서, 산성 지지물의 양이 일반식(Ⅱ) 또는 화합물의 몰당 10 내지 20몰인 상기 방법.
- 제6항 또는 7항에 있어서, 산성 지지물이 포스포러스옥시클로라이드, 포스포러스 펜타클로라이드, 포스포러스트리클로라이드, 염화티오닐, 농황산 또는 폴리포스포러스산인 상기 방법.
- 제1항, 제2항, 제3항, 제4항, 제5항, 제6항, 제7항 또는 제8항중 어느 한 항에 있어서, 가수분해를 촉매 존재하에 실온 내지 200℃에서 수행하는 상기 방법.
- 제9항에 있어서, 가수분해를 50 내지 150℃에서 수행하는 상기 방법.
- 제9항 또는 제10항에 있어서 촉매가 염기성화합물인 상기 방법.
- 제9항 또는 제10항에 있어서, 촉매가 광산 또는 유기산인 상기 방법.
- 제9항, 제10항, 제11항 또는 제12항에 있어서, 가수분해가 용매중에 수행되는 상기 방법.
- 제1항에 있어서, 일반식(Ⅰ)의 벤조헤테로사이클릭 화합물이 일반식(Ⅱ)의 벤조헤테로사이클릭 화합물을 폐환시켜 제조되는 상기 방법.
- 제1항에 있어서, 일반식(Ⅰ)의 벤조헤테로사이클릭 화합물이 일반식(Ⅱ)의 벤조헤테로사이클릭 화합물을 폐환시켜 제조되는 상기 방법.
- 제14항에 있어서, 용매중에 일반식(Ⅱ)의 화합물을 약 100 내지 250℃ 온도로 가열시켜 폐환을 수행하는 상기 방법.
- 제14항에 있어서, 반응을 150 내지 200℃에서 수행하는 상기 방법.
- 제14항에 있어서, 일반식(Ⅱ) 화합물의 몰당 적어도 1몰의 과량의 산성 지지몰을 사용하여 폐환을 약 100 내지 150℃에서 수행하는 상기 방법.
- 제14항에 있어서, 산성 지지물의 양이 일반식(Ⅱ)화합물의 몰당 10 내지 20몰인 상기 방법.
- 제15항에 있어서, 용매중에 일반식(Ⅲ)화합물을 약 100 내지 250℃ 온도로 가열시켜 폐환을 수행하는 상기 방법.
- 제15항에 있어서, 반응을 150 내지 200℃에서 수행하는 상기 방법.
- 제15항에 있어서, 일반식(Ⅲ)화합물의 몰당 적어도 1몰의 과량의 산성 지지물을 사용하여 폐환을 약 100 내지 150℃에서 약 0.5 내지 6시간동안 수행하는 상기 방법.
- 제15항에 있어서, 산성 지지물의 양이 일반식(Ⅲ) 화합물의 몰당 10 내지 20몰인 상기 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55179949A JPS57102887A (en) | 1980-12-18 | 1980-12-18 | Preparation of benzo(ij)quinolizine-2-carboxylic acid derivative |
| JP179949 | 1980-12-18 | ||
| JP152451/81 | 1981-09-25 | ||
| JP15245181A JPS5855484A (ja) | 1981-09-25 | 1981-09-25 | ピロロ〔３，２，１−「あい」「じえゞ」〕キノリン−５−カルボン酸誘導体の製造法 |
| JP152451 | 1981-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007647A true KR830007647A (ko) | 1983-11-04 |
| KR880001634B1 KR880001634B1 (ko) | 1988-09-03 |
Family
ID=26481369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004999A KR880001634B1 (ko) | 1980-12-18 | 1981-12-17 | 벤조 헤테로사이클릭 화합물의 제조방법 |
Country Status (9)
| Country | Link |
|---|---|
| KR (1) | KR880001634B1 (ko) |
| AR (1) | AR231723A1 (ko) |
| AT (1) | AT380250B (ko) |
| CA (1) | CA1183535A (ko) |
| ES (1) | ES508647A0 (ko) |
| FR (1) | FR2496662B1 (ko) |
| GB (1) | GB2091726B (ko) |
| PT (1) | PT74145B (ko) |
| SU (1) | SU1428201A3 (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| US4472406A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
| JPS59137482A (ja) * | 1983-01-26 | 1984-08-07 | Otsuka Pharmaceut Co Ltd | ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体 |
| JPS59155381A (ja) * | 1983-02-22 | 1984-09-04 | Kyorin Pharmaceut Co Ltd | ベンゾキノリジンカルボン酸誘導体及びその製造法 |
| ATE81975T1 (de) * | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
| EP0185429A1 (en) * | 1984-12-21 | 1986-06-25 | Duphar International Research B.V | New bicyclic heteroaryl piperazines |
| AU585981B2 (en) * | 1985-05-24 | 1989-06-29 | Tokyo Tanabe Company Limited | Benzo (IJ) quinolizine-2-carboxylic acid derivatives, the salts and their hydrates, pharmaceutical compositions thereof, and processes for preparing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| DE2914258A1 (de) * | 1978-04-12 | 1979-10-25 | Otsuka Pharma Co Ltd | Piperazinylbenzoheterozyklische verbindungen, verfahren zu deren herstellung und mittel, welche diese enthalten |
-
1981
- 1981-12-17 AT AT0540181A patent/AT380250B/de not_active IP Right Cessation
- 1981-12-17 PT PT74145A patent/PT74145B/pt not_active IP Right Cessation
- 1981-12-17 SU SU813367435A patent/SU1428201A3/ru active
- 1981-12-17 KR KR1019810004999A patent/KR880001634B1/ko active
- 1981-12-18 ES ES508647A patent/ES508647A0/es active Granted
- 1981-12-18 FR FR818123744A patent/FR2496662B1/fr not_active Expired
- 1981-12-18 CA CA000392721A patent/CA1183535A/en not_active Expired
- 1981-12-18 GB GB8138320A patent/GB2091726B/en not_active Expired
- 1981-12-18 AR AR287862A patent/AR231723A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1428201A3 (ru) | 1988-09-30 |
| ES8304972A1 (es) | 1983-04-01 |
| KR880001634B1 (ko) | 1988-09-03 |
| AR231723A1 (es) | 1985-02-28 |
| FR2496662A1 (fr) | 1982-06-25 |
| PT74145B (en) | 1983-05-30 |
| PT74145A (en) | 1982-01-01 |
| FR2496662B1 (fr) | 1985-07-26 |
| AT380250B (de) | 1986-04-25 |
| ES508647A0 (es) | 1983-04-01 |
| ATA540181A (de) | 1985-09-15 |
| GB2091726B (en) | 1985-02-20 |
| CA1183535A (en) | 1985-03-05 |
| GB2091726A (en) | 1982-08-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR870003989A (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
| KR840009063A (ko) | 펜에타놀아민 유도체 제조방법 | |
| KR850003890A (ko) | 1H-이미다조[4,5c]-퀴놀린-4-아민의 제조방법 | |
| KR850001199A (ko) | 1,8-나프티리딘 유도체의 제조법 | |
| KR840005450A (ko) | 말론산에스테르의 이성화 방법 | |
| KR860004025A (ko) | 퀴놀론 카복실산의 제조방법 | |
| KR840004102A (ko) | 퀴놀린 화합물의 제조방법 | |
| KR840000508A (ko) | 4-아닐리노피리미딘 유도체의 제조방법 | |
| KR830007647A (ko) | 벤조헤테로사이클릭 화합물의 제조방법 | |
| KR940703807A (ko) | 22-옥사콜레칼시페롤 유도체 및 그의 제조방법(22-oxacholecalciferol derivative and production thereof) | |
| KR860001065A (ko) | 4-아세톡시-3-히드록시에틸아제티진-2-온유도체의 제조방법 | |
| KR840001555A (ko) | 치환된 2-페닐-2-(피리딜욕시)-에틸아민과 그의 등 배전자화합물 및 그들의 산부가염을 제조하는 방법 | |
| KR840006476A (ko) | 3-페녹시벤질 2-(4-알콕시페닐)-2-메틸프로필 에테르의 제조방법 | |
| KR890701564A (ko) | 퀴놀린 카복실산 유도체를 제조하는 방법 | |
| KR860008135A (ko) | 아미노케톤 유도체의 제조방법 | |
| KR870002069A (ko) | 2-(3,5-디알킬-4-히드록시페닐) 인돌 유도체의 제조방법 | |
| KR830007554A (ko) | 인돌리논의 제조방법 | |
| KR830004320A (ko) | 퀴나졸린 유도체의 제조방법 | |
| KR860001073A (ko) | 이미다졸린의 제조방법 | |
| KR840005723A (ko) | 티아졸유도체의 제조방법 | |
| KR900011751A (ko) | 선택적 에테르화 반응 | |
| KR900014355A (ko) | 티오펜-2,5-디카르복실산디에스테르, 테트라하이드로티오펜-2,5-디카르복실산디에스테르 및 디벤즈옥사졸일 티오펜의 제조방법 | |
| KR830007639A (ko) | 락탐 화합물의 제조방법 | |
| KR840005107A (ko) | 피리미디온 및 그의 산부가염의 제조방법 | |
| KR840000551A (ko) | 이미다조[1, 2-a]피리미딘의 제조방법 |