KR830009098A - 6-치환된 헥사하이드로인다졸로 또는 헥사하이드로 이소인돌로 이소퀴놀린의 제조방법 - Google Patents
6-치환된 헥사하이드로인다졸로 또는 헥사하이드로 이소인돌로 이소퀴놀린의 제조방법 Download PDFInfo
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- KR830009098A KR830009098A KR1019820001256A KR820001256A KR830009098A KR 830009098 A KR830009098 A KR 830009098A KR 1019820001256 A KR1019820001256 A KR 1019820001256A KR 820001256 A KR820001256 A KR 820001256A KR 830009098 A KR830009098 A KR 830009098A
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- hexahydro
- isoquinoline
- dimethoxy
- indazolo
- propyl
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- 238000000034 method Methods 0.000 title claims 10
- SVTHIBVHMIFFMN-UHFFFAOYSA-N 2,3,3a,3b,4,5-hexahydro-1h-isoindolo[4,5-h]isoquinoline Chemical compound C1=NC=C2C3=CC=C4CNCC4C3CCC2=C1 SVTHIBVHMIFFMN-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- -1 (C 1 -C 2 ) alkyl anhydride Chemical class 0.000 claims 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- LPJPYEYQJAYAPV-UHFFFAOYSA-N 7,8-dimethoxy-2-methyl-2,11,12-triazatetracyclo[7.6.1.05,16.010,14]hexadeca-5,7,9(16),10(14),12-pentaene Chemical group C1=2C3=C(OC)C(OC)=CC=2CCN(C)C1CC1=C3NN=C1 LPJPYEYQJAYAPV-UHFFFAOYSA-N 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- MZPZAIVRISPTJQ-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-isoindole Chemical compound C1CCC2CNCC2=C1 MZPZAIVRISPTJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- CCKXLQHALQZTIX-UHFFFAOYSA-N 8-(dimethylaminomethylidene)-5,6-dimethoxy-1-methyl-2,3,9,9a-tetrahydrobenzo[de]quinolin-7-one Chemical compound C1C(=CN(C)C)C(=O)C2=C(OC)C(OC)=CC3=C2C1N(C)CC3 CCKXLQHALQZTIX-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- GZWNUORNEQHOAW-UHFFFAOYSA-M potassium;2-aminoacetate Chemical compound [K+].NCC([O-])=O GZWNUORNEQHOAW-UHFFFAOYSA-M 0.000 claims 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- CZXDLPMZPSFMNI-UHFFFAOYSA-N 2-methyl-2,11,12-triazatetracyclo[7.6.1.05,16.010,14]hexadeca-5(16),6,8,10(14),12-pentaene Chemical compound C1=2NN=CC=2CC2N(C)CCC3=CC=CC1=C32 CZXDLPMZPSFMNI-UHFFFAOYSA-N 0.000 claims 1
- IGROWBZMFLYVBA-UHFFFAOYSA-N 2-methyl-2,11,12-triazatetracyclo[7.6.1.05,16.010,14]hexadeca-5,7,9(16),10(14),12-pentaene-7,8-diol Chemical compound OC1=C(C=C2CCN(C3C2=C1C1=NNC=C1C3)C)O IGROWBZMFLYVBA-UHFFFAOYSA-N 0.000 claims 1
- JRWOJDBPEPPLIB-UHFFFAOYSA-N 7,8-dimethoxy-2-propyl-2,11,12-triazatetracyclo[7.6.1.05,16.010,14]hexadeca-5,7,9(16),10(14),12-pentaene Chemical compound C1=2NN=CC=2CC2N(CCC)CCC3=CC(OC)=C(OC)C1=C32 JRWOJDBPEPPLIB-UHFFFAOYSA-N 0.000 claims 1
- NILPKFGHMLCBHP-UHFFFAOYSA-N 8-(dimethylaminomethylidene)-1-methyl-2,3,9,9a-tetrahydrobenzo[de]quinolin-7-one Chemical compound CN1CCC2=CC=CC3=C2C1CC(=CN(C)C)C3=O NILPKFGHMLCBHP-UHFFFAOYSA-N 0.000 claims 1
- OJGFGGBETOWJKX-UHFFFAOYSA-N 8-(dimethylaminomethylidene)-5,6-dimethoxy-1-propyl-2,3,9,9a-tetrahydrobenzo[de]quinolin-7-one Chemical compound O=C1C(=CN(C)C)CC2N(CCC)CCC3=CC(OC)=C(OC)C1=C32 OJGFGGBETOWJKX-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
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- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- 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
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- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
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- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 8-디메틸아미노메틸렌 유도체를 Z가또는인 경우에는 불화성용매 중에서 R6-NH2(이때 R6는 NH2-)와 반응시키고, Z가 (C1-C2)알킬인 경우에는 R6-NH2(이때 R6는이고 M은 K 또는 Na) 및 (C1-C2) 알킬 안하이드리드와 반응시키고, R3가,C2) 알킬인 경우에는 임의로 가수분해하여 R3가 H인 일반식(I)의 화합물을 수득하고, R1및/또는 R2가 (C1-C3) 알콕시인 화합물을 임의로 탈알킬화하여 R1및/또는 R2가 OH인 일반식(I)의 화합물을 수득하고, R이 H인 경우에는 임의로 환원적으로 알킬화하여 R이 (C1-C3) 알킬 또는 알릴인 화합물을 수득함을 특징으로 하여 일반식(I)의 6-치환된 헥사하이드로인다졸로 또는 헥사하이드로 이소인돌로 이소퀴놀린 또는 그의 염을 제조하는 방법.상기 식중R은 H, (C1-C3) 알킬, 알릴 또는 벤질이고R1및 R2는 독립적으로 H, OH 또는 (C1-C3)-알콕시이며, 단, R1또는 R2가 OH일 경우에는 나머지 R1또는 R2가 (C1-C2) 알콕시가 될 수 없고,Z는이며R3는 H 또는알킬이고, 점선은 7a-10a 또는 7a-8에서 1개의 이중결합이 존재함을 나타내며,R4및 R5는 독립적으로 H 또는 (C1-C3) 알콕시이다.
- 제1항에 있어서, 제1항에서 정의된 일반식(II)의 화합물을 무수 하이드라진과 불활성용매 중에서 반응시킴을 특징으로 하여 Z가또는인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 제1항에서 정의된 일반식(II)의 화합물을 알카리금속 글리시네이트 및 (C1-C2) 알킬 안하이드리드와 반응시킴을 특징으로 하여 Z가 (C1-C2) 알킬인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 1-메틸-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킴을 특징으로 하여 6-메틸-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 6-메틸-4,5,6,6aa,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-n-프로필-7-옥소-8-디메틸-아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킴을 특징으로하여 6-n-프로필-4,5,6,6,a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 6-n-프로필-4,5,6,6aa,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-벤질-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9,a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킴을 특징으로 하여 1,2-디메톡시-6-벤질-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 1,2-디메톡시-6-벤질-4,5,6,6,a,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-메틸-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킴을 특징으로 하여 1,2-디메톡시-6-메틸-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 1,2-디메톡시-6-메틸-4,5,6,6a,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-메틸-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킨후, 생성물을 HBr과 빙초산중에서 반응시킴을 특징으로 하여 1,2-디메톡시-6-메틸-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 1,2-디하이드록시-6-메틸-4,5,6,6a,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-n-프로필-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킴을 특징으로 하여 1,2-디메톡시-6-n-프로필-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 1,2-디메톡시-6-n-프로필-4,5,6,6a,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-n-프로필-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 무수 하이드라진과 메탄올중에서 반응시킨후 생성물을 HBr과 빙초산중에서 반응시킴을 특징으로 하여 1,2-하이드록시-6-n-프로필-4,5,6,6a,7,9-헥사하이드로 인다졸로[7,6,5-ij] 이소퀴놀린 및 1,2-디하이드록시-6-n-프로필-4,5,6,6a,7,10-헥사하이드로 인다졸로[7,6,5-ij]이소퀴놀린의 토오토오머 혼합물을 제조하는 방법.
- 제1항에 있어서, 1-n-프로필-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 칼륨 글리시네이트 및 무수초산과 반응시킴을 특징으로 하여 1,2-디메톡시-6-n-프로필-9-아세틸-4,5,6,6a,7,9-헥사하이드로 이소인돌[4,5,6-ij] 이소퀴놀린을 제조하는 방법.
- 제1항에 있어서, 1-n-프로필-5,6-디메톡시-7-옥소-8-디메틸아미노메틸렌-2,3,7,8,9,9a-헥사하이드로-1H-벤조[데]퀴놀린을 칼륨 글리시네이트 및 무수초산과 반응시킨후 생성물을 나트륨 에톡시드와 반응시킴을 특징으로 하여 1,2-디메톡시-6-n-프로필-4,5,6,6a,7,9-헥사하이드로 이소인돌[4,5,6-ij] 이소퀴놀린을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24704781A | 1981-03-24 | 1981-03-24 | |
| US247047 | 1981-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830009098A true KR830009098A (ko) | 1983-12-17 |
Family
ID=22933334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820001256A KR830009098A (ko) | 1981-03-24 | 1982-03-24 | 6-치환된 헥사하이드로인다졸로 또는 헥사하이드로 이소인돌로 이소퀴놀린의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP0151319B1 (ko) |
| JP (1) | JPS57171993A (ko) |
| KR (1) | KR830009098A (ko) |
| AT (2) | ATE33641T1 (ko) |
| AU (1) | AU8181482A (ko) |
| CA (3) | CA1182457A (ko) |
| DD (1) | DD202161A5 (ko) |
| DE (2) | DE3278359D1 (ko) |
| DK (1) | DK130282A (ko) |
| ES (2) | ES510695A0 (ko) |
| FI (1) | FI820938L (ko) |
| GB (2) | GB2095255B (ko) |
| GR (1) | GR75926B (ko) |
| HU (1) | HU189572B (ko) |
| IL (3) | IL65269A0 (ko) |
| PH (2) | PH18370A (ko) |
| PL (2) | PL240285A1 (ko) |
| PT (1) | PT74612B (ko) |
| RO (2) | RO82502A (ko) |
| SU (1) | SU1189349A3 (ko) |
| ZA (1) | ZA821805B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3624607A1 (de) * | 1986-07-21 | 1988-01-28 | Boehringer Ingelheim Kg | Neue tetrahydrobenzothiazolo-chinoline ihre herstellung und verwendung |
| CN107434781A (zh) * | 2016-05-27 | 2017-12-05 | 河南工业大学 | 一种1-烯基-异喹啉衍生物的制备方法及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198415A (en) * | 1979-01-22 | 1980-04-15 | Eli Lilly And Company | Prolactin inhibiting octahydro pyrazolo[3,4-g]quinolines |
| CA1131227A (en) * | 1979-01-22 | 1982-09-07 | Nicholas J. Bach | Octahydro-2h-pyrrolo (3,4,-g) quinolines |
| US4201862A (en) * | 1979-03-16 | 1980-05-06 | Eli Lilly And Company | 2-Azaergolines and 2-aza-8(or 9)-ergolenes |
-
1982
- 1982-03-16 IL IL65269A patent/IL65269A0/xx unknown
- 1982-03-17 ZA ZA821805A patent/ZA821805B/xx unknown
- 1982-03-17 CA CA000398593A patent/CA1182457A/en not_active Expired
- 1982-03-18 FI FI820938A patent/FI820938L/fi not_active Application Discontinuation
- 1982-03-18 RO RO82106957A patent/RO82502A/ro unknown
- 1982-03-18 RO RO111501A patent/RO86517B/ro unknown
- 1982-03-19 PH PH27025A patent/PH18370A/en unknown
- 1982-03-19 PT PT74612A patent/PT74612B/pt unknown
- 1982-03-23 GB GB8208503A patent/GB2095255B/en not_active Expired
- 1982-03-23 AU AU81814/82A patent/AU8181482A/en not_active Abandoned
- 1982-03-23 EP EP84201377A patent/EP0151319B1/en not_active Expired
- 1982-03-23 EP EP82301483A patent/EP0061341B1/en not_active Expired
- 1982-03-23 DE DE8484201377T patent/DE3278359D1/de not_active Expired
- 1982-03-23 HU HU82878A patent/HU189572B/hu unknown
- 1982-03-23 GR GR67692A patent/GR75926B/el unknown
- 1982-03-23 PL PL24028582A patent/PL240285A1/xx unknown
- 1982-03-23 AT AT84201377T patent/ATE33641T1/de not_active IP Right Cessation
- 1982-03-23 SU SU823408197A patent/SU1189349A3/ru active
- 1982-03-23 DE DE8282301483T patent/DE3270838D1/de not_active Expired
- 1982-03-23 DK DK130282A patent/DK130282A/da not_active Application Discontinuation
- 1982-03-23 ES ES510695A patent/ES510695A0/es active Granted
- 1982-03-23 AT AT82301483T patent/ATE19517T1/de not_active IP Right Cessation
- 1982-03-23 PL PL23558282A patent/PL235582A1/xx unknown
- 1982-03-24 JP JP57048077A patent/JPS57171993A/ja active Pending
- 1982-03-24 KR KR1019820001256A patent/KR830009098A/ko unknown
- 1982-03-24 DD DD82238403A patent/DD202161A5/de unknown
-
1983
- 1983-01-17 ES ES519056A patent/ES8403459A1/es not_active Expired
- 1983-06-30 PH PH29152A patent/PH18719A/en unknown
-
1984
- 1984-06-27 CA CA000457635A patent/CA1187883A/en not_active Expired
- 1984-06-27 CA CA000457636A patent/CA1187884A/en not_active Expired
- 1984-10-04 GB GB848425095A patent/GB8425095D0/en active Pending
-
1985
- 1985-04-08 IL IL74836A patent/IL74836A0/xx unknown
- 1985-04-08 IL IL74837A patent/IL74837A0/xx unknown
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