KR850000440A - 헥사하이드로피롤로[2,1-a]이소퀴놀린 유도체의 제조방법 - Google Patents
헥사하이드로피롤로[2,1-a]이소퀴놀린 유도체의 제조방법 Download PDFInfo
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- KR850000440A KR850000440A KR1019840003577A KR840003577A KR850000440A KR 850000440 A KR850000440 A KR 850000440A KR 1019840003577 A KR1019840003577 A KR 1019840003577A KR 840003577 A KR840003577 A KR 840003577A KR 850000440 A KR850000440 A KR 850000440A
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- Prior art keywords
- isoquinoline
- hexahydro
- formula
- carbon atoms
- hydrogen
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- 238000000034 method Methods 0.000 title claims 11
- SMMNWJYSCYKBRA-UHFFFAOYSA-N 1,2,3,5,6,6a-hexahydropyrrolo[2,1-a]isoquinoline Chemical class C1CC2C=CC=CC2=C2N1CCC2 SMMNWJYSCYKBRA-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- -1 methylenedioxy Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000003951 lactams Chemical class 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- HBMUMVMGBLMQJT-UHFFFAOYSA-N pyrrolo[2,1-a]isoquinoline Chemical compound C12=CC=CC=C2C=CN2C1=CC=C2 HBMUMVMGBLMQJT-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OTXWJRQMWUWVPF-UHFFFAOYSA-N 6-phenyl-2,3,5,10b-tetrahydro-1h-pyrrolo[2,1-a]isoquinolin-6-ol Chemical compound C1N2CCCC2C2=CC=CC=C2C1(O)C1=CC=CC=C1 OTXWJRQMWUWVPF-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- 229910010277 boron hydride Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 150000007975 iminium salts Chemical class 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- 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, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- 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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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- (i) 다음 일반식(IV-A)의 락탐을 환원시키거나, (ii) R3가 수소인 일반식(I)의 화합물을 제조하기 위해서는, 다음 일반식(XIV-A)의 락탐을 환원시키거나, (iii) R2가 수소인 일반식(I)의 화합물을 제조하기 위해서는, 다음 일반식(VII-A)의 아미노 알콜을 폐환시키거나, (iv) R1이 수소인 일반식(I)화합물을 제조하기 위해서는 다음 일반식(XIX-A)의 이미늄 염을 환원시키거나, R1이 수소가 아닌 일반식(I)의 화합물을 제조하기 위해서는 일반식(XIX-A)의 이미늄염을 R1-그리나드 화합물과 반응시킴을 특징으로 하여 일반식(I)의 화합물, 그의 디아스테레오머 및 무독한 약제학적으로 허용되는 산부가염을 제조하는 방법.상기식에서, R1은 수소 또는 탄소수 1내지 4의 저급알킬이고, R2는 수소, 탄소수 1내지 4의 저급알킬, 플루오로, 하이드록시, 또는 탄소수 1내지 4의 저급알콕시이며, R3는 수소, 메틸 또는 페닐이고, R4와 R5는 같거나 다르며 둘다 수소이거나 또는 각각 수소 또는 탄소수 1내지 4를 갖는 저급알킬 그룹중에서 선택된 것이고, R6와 R7은 같거나 다르며, 각각은 수소, 탄소수 1내지 4의 저급알킬, 탄소수 1내지 4의 저급알콕시, 하이드록시 또는 할로겐 그룹중에서 선택된 것이거나 또는 함께 메틸렌디옥시를 나타내며, A는 하기 일반식(1),(2) 또는(3)의 단위 그룹중에서 선택된 것이고이때, 일반식(1)의 벤젠 단위 중에서 R8및 R9는 수소, 탄소수 1 내지 6의 저급알킬, 탄소수 1내지 4의 퍼플루오로(저급)알킬, 하이드록시, 탄소수 1내지 4의 저급알콕시, 탄소수 1내지 5의 카브(저급)알콕시, 탄소수 1내지 5의 저급아실아미노, 벤조일아미노, 시아노, 카복사마이도, 탄소수 1내지 5의 저급아실, 탄소수 1내지 4의 저급알킬티오, 탄소수 1내지 4의 저급알킬설포닐, 니트로, 아미노, 각각의 알킬중에 탄소수 1내지 4의 저급알킬-또는 디(저급)알킬-아미노 또는 할로겐 그룹중에서 선택된 것이고, 일반식(2)의 헤테로방향족 단위중에서 X는 산소 또는 황이며, 일반식(3)의 사이클로알킬 단위중에서 n은 0내지 2이고, 일반식(1),(2) 및 (3)의 단위 그룹은 어느 탄소원자에서나 부착될 수 있으며, X1은 음이은이다.
- 제1항의 (i)에 있어서, 환원 반응을 알루미늄 또는 보론 하이드리드를 사용하여 수행하는 방법.
- 제1항의 (ii)에 있어서, 환원반응 르위스산-타입 하이드리드 시약을 사용하여 수행하는 방법.
- 제1항의 (iii)에 있어서, 폐환반응을 산촉매를 사용하여 수행하는 방법.
- 제1항의 (iv)에 있어서, X1이 클로로인 일반식(XIX-A)화합물의 이미늄염을 사용하는 방법.
- 제1항의 (iv) 또는 5항에 있어서, 환원 반응을 NaBH4또는 LiAIH4를 사용하여 수행하는 방법.
- 제1항의 (iv) 또는 5항에 있어서, R1-그리나드 화합물로서 메틸 마그네슘 브로마이드를 사용하는 방법.
- 제1항에 있어서, R3, R4및 R5가 모두 수소인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R2,R3,R4,R5,R6및 R7이 수소이고 A가 일반식(1)의 단위인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, [6α, 10bβ] - 1,2,3,5,6,10b-헥사하이드로-10b-메틸-6-페닐-피롤로[2,1-a]이소퀴놀린; [6α,10bβ]- 1,2,3,5,6,10b-헥사하이드로-6-페닐피롤로[2a,1-a]이소퀴놀린; 6α-(3,4-디클로로페닐)-1,2,3,5,6,10bα-헥사하이드로피롤로-[2,1-a]이소퀴놀린; 1,2,3,5,6,10bβ - 헥사하이드로 - 6-메틸-6α-페닐피롤로[2,1-a]이소퀴놀린; [6α, 10bβ]-1,2,3,5,6,10b - 헥사하이드로-8,9-디하이드록시-6-페닐-피롤로[2,1-a]이소퀴놀린; [6α,10bα]-6-사이클로헥실-1,2,3,5,6,10b-헥사하이드로피롤로[2,1-a]이소퀴 놀린; [6α,10bβ]-6-(4-클로로페닐)-1,2,3,5,6,10b-헥사하이드로-피롤로[2,1-a]이소퀴놀린; 6α-(4-클로로페닐)-1,2,3,5,6,10bα-헥사하이드로-피롤로[2, 1-a]이소퀴놀린; 1,2,3,5,6,10bβ-헥사하이드로-6α-(4-메톡시페닐)피롤로[2,1-a]이소퀴놀린; 1,2,3,5,6,10b-헥사하이드로-6-페닐피롤로[2,1-a]이소퀴놀린-6-올; 4-(1,2,3,5,6,10bβ-헥사하이드로피롤로[2,1-a]이소퀴놀린-6α-일)벤젠-1,2-디올; 1,2,3,5,6,10bβ-헥사하이드로-6α-(4-니트로페닐)피롤로[2,1-a]이소퀴놀린; 1,2,3,5,6,10bβ-헥사하이드로-6α-(3-메톡시페닐)피롤로[2,1-a]이소퀴놀린; 3-(1,2,3,5,6,10bβ-헥사하이드로피롤로[2,1-a]이소퀴놀린-6a-일)페놀; 1,2,3,5,6,10bβ-헥사하이드로-6α-(3,4-디메톡시페닐)피롤로-[2,1-a]이소퀴놀린; 1,2,3,5,6,10bβ-헥사하이드로-7-메톡시-6α-페닐피롤로 [2,1-a]-이소퀴놀린; 4-(1,2,3,5,6,10bα-헥사하이드로피롤로[2,1-a]이소퀴놀린-6a-일)벤젠 아민, 1,2,3,5,6,10bβ-헥사하이드로-6α-[(3-트리플루오로메틸)페닐]-피롤로[2,1-a]이소퀴놀린; 9-플루오로-6α-(4-플루오로페닐)-1,2,3,5,6,10b-헥사하이드로-10bβ-메틸피롤로[2,1-a]이소퀴놀린; [6α, 10bβ]-6-(2-클로로페닐)-1,2,3,5,6,10b-헥사하이드로-피롤로[2,1-a]이소퀴놀린; 또는 1,2,3,5,6,10bβ-헥사하이드로-6α-(4-메틸티오페닐)-피롤로[2,1-a]이소퀴놀린을 유기염기 또는 산부가염의 형태로 제조하는 방법.
- 제1항에 있어서, 1,2,3,5,6,10bβ-헥사하이드로-6α-[(3-트리플루오로메틸)페닐]피롤로[2,1-a]이소퀴놀린의 유기염기 또는 산부가염을 제조하는 방법.
- 제1항에 있어서, [6α, 10bβ]-6-(2-클로로페닐)-1,2,3,5,10b-헥사하이드로피롤로[2,1-a]이소퀴놀린의 유리염기 또는 산부가염을 제조하는 방법.
- 제1항에 있어서, 1,2,3,5,6,10bβ -헥사하이드로-6α-(4-메틸디오페닐)피롤로[2,1-a]이소퀴놀린의 유리염기 또는 산부가염을 제조하는 방법.
- 제1항에 있어서, 10bβ형태의 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 일반식(1)의 벤젠단위에서 R8및 R9가 수소, 탄소수 1내지 6의 저급알킬, 탄소수 1내지 4의 퍼플루오로(저급)알킬, 하이드록시, 탄소수 1내지 4의 저급알콕시, 탄소수 1내지 5의 카브(저급)알콕시, 탄소수 1내지 5의 저급 아실아미노, 탄소수 1내지 5의 저급아실, 탄소수 1내지 4의 저급알킬티오, 탄소수 1내지 4의 저급 알킬설포닐, 니트로, 아미노, 탄소수 1내지 4의 저급알킬-또는 디(저급)알킬-아미노 또는 할로겐 중에서 선택되는 일반식(I)의 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50725083A | 1983-06-23 | 1983-06-23 | |
| US507,250 | 1983-06-23 | ||
| US507250 | 1983-06-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850000440A true KR850000440A (ko) | 1985-02-27 |
| KR910002564B1 KR910002564B1 (ko) | 1991-04-26 |
Family
ID=24017860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840003577A KR910002564B1 (ko) | 1983-06-23 | 1984-06-23 | 헥사하이드로피롤로[2,1-a]이소퀴놀린 유도체의 제조방법 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0130069B1 (ko) |
| JP (1) | JPS6069082A (ko) |
| KR (1) | KR910002564B1 (ko) |
| AT (1) | ATE59041T1 (ko) |
| AU (1) | AU563990B2 (ko) |
| CA (1) | CA1253155A (ko) |
| DE (1) | DE3483735D1 (ko) |
| DK (1) | DK305184A (ko) |
| ES (1) | ES533657A0 (ko) |
| FI (1) | FI76798C (ko) |
| HK (1) | HK54891A (ko) |
| HU (1) | HU193937B (ko) |
| NO (1) | NO164474C (ko) |
| NZ (1) | NZ208480A (ko) |
| SG (1) | SG44391G (ko) |
| ZA (1) | ZA844402B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572911A (en) * | 1984-08-02 | 1986-02-25 | Mcneilab, Inc. | Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates |
| DE3717395A1 (de) * | 1987-05-23 | 1988-12-08 | Basf Ag | 5-phenyl-1,2,3a,4,5,9b-hexahydro-3h-benz(e) indole, ihre herstellung und verwendung als arzneimittel |
| GB8718980D0 (en) * | 1987-08-11 | 1987-09-16 | May & Baker Ltd | Compositions of matter |
| GB9326699D0 (en) * | 1993-12-22 | 1994-03-02 | Celltech Ltd | Chemical compounds |
| WO2006138604A1 (en) | 2005-06-17 | 2006-12-28 | Janssen Pharmaceutica N.V. | Hexahydro-pyrrolo-isoquinoline compounds for the treatment of cns disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE690792A (ko) * | 1966-12-07 | 1967-05-16 | ||
| CH527194A (de) * | 1970-01-06 | 1972-08-31 | Hoffmann La Roche | Verfahren zur Herstellung von Isochinolin-Derivaten |
-
1984
- 1984-06-11 ZA ZA844402A patent/ZA844402B/xx unknown
- 1984-06-12 NZ NZ208480A patent/NZ208480A/en unknown
- 1984-06-12 NO NO842345A patent/NO164474C/no unknown
- 1984-06-14 CA CA000456578A patent/CA1253155A/en not_active Expired
- 1984-06-21 FI FI842533A patent/FI76798C/fi not_active IP Right Cessation
- 1984-06-22 EP EP84304247A patent/EP0130069B1/en not_active Expired - Lifetime
- 1984-06-22 DE DE8484304247T patent/DE3483735D1/de not_active Expired - Fee Related
- 1984-06-22 DK DK305184A patent/DK305184A/da unknown
- 1984-06-22 AU AU29777/84A patent/AU563990B2/en not_active Ceased
- 1984-06-22 HU HU842443A patent/HU193937B/hu not_active IP Right Cessation
- 1984-06-22 AT AT84304247T patent/ATE59041T1/de not_active IP Right Cessation
- 1984-06-22 ES ES533657A patent/ES533657A0/es active Granted
- 1984-06-23 KR KR1019840003577A patent/KR910002564B1/ko not_active IP Right Cessation
- 1984-06-23 JP JP59129917A patent/JPS6069082A/ja active Pending
-
1991
- 1991-06-14 SG SG44391A patent/SG44391G/en unknown
- 1991-07-18 HK HK548/91A patent/HK54891A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE59041T1 (de) | 1990-12-15 |
| SG44391G (en) | 1991-07-26 |
| HUT34478A (en) | 1985-03-28 |
| EP0130069A2 (en) | 1985-01-02 |
| HU193937B (en) | 1987-12-28 |
| EP0130069B1 (en) | 1990-12-12 |
| NO842345L (no) | 1984-12-27 |
| DE3483735D1 (en) | 1991-01-24 |
| CA1253155A (en) | 1989-04-25 |
| EP0130069A3 (en) | 1985-09-11 |
| KR910002564B1 (ko) | 1991-04-26 |
| HK54891A (en) | 1991-07-26 |
| FI842533A (fi) | 1984-12-24 |
| FI76798B (fi) | 1988-08-31 |
| ES8602676A1 (es) | 1985-10-01 |
| DK305184A (da) | 1984-12-24 |
| NO164474B (no) | 1990-07-02 |
| FI76798C (fi) | 1988-12-12 |
| FI842533A0 (fi) | 1984-06-21 |
| JPS6069082A (ja) | 1985-04-19 |
| NO164474C (no) | 1990-10-10 |
| NZ208480A (en) | 1986-08-08 |
| ZA844402B (en) | 1986-01-29 |
| DK305184D0 (da) | 1984-06-22 |
| AU563990B2 (en) | 1987-07-30 |
| ES533657A0 (es) | 1985-10-01 |
| AU2977784A (en) | 1985-01-03 |
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