KR840004111A - 중추신경계 약제인 치환된 헥사하이드로피롤로 -[1, 2-a]-퀴놀린, 헥사하이드로-1H-피리도[1, 2-a]-퀴놀린, 헥사하이드로벤조-[e]인덴 및 옥타하이드로페난트렌의 제조방법 - Google Patents
중추신경계 약제인 치환된 헥사하이드로피롤로 -[1, 2-a]-퀴놀린, 헥사하이드로-1H-피리도[1, 2-a]-퀴놀린, 헥사하이드로벤조-[e]인덴 및 옥타하이드로페난트렌의 제조방법 Download PDFInfo
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- KR840004111A KR840004111A KR1019830001021A KR830001021A KR840004111A KR 840004111 A KR840004111 A KR 840004111A KR 1019830001021 A KR1019830001021 A KR 1019830001021A KR 830001021 A KR830001021 A KR 830001021A KR 840004111 A KR840004111 A KR 840004111A
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- compound
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- alkyl
- quinoline
- hydrogen
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- KUHKFJPHPOPHDT-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline Chemical class C1CC2=CC=CC=C2N2C1CCC2 KUHKFJPHPOPHDT-UHFFFAOYSA-N 0.000 title 1
- BCVPDPPVMKVZKC-UHFFFAOYSA-N 2,3,3a,4,5,9b-hexahydro-1h-cyclopenta[a]naphthalene Chemical class C1CC2=CC=CC=C2C2C1CCC2 BCVPDPPVMKVZKC-UHFFFAOYSA-N 0.000 title 1
- BBDSHWCHKVXFOM-UHFFFAOYSA-N 2,3,4,4a,5,6-hexahydro-1h-benzo[c]quinolizine Chemical class C1=CC=C2N3CCCCC3CCC2=C1 BBDSHWCHKVXFOM-UHFFFAOYSA-N 0.000 title 1
- 229940125693 central nervous system agent Drugs 0.000 title 1
- 239000003576 central nervous system agent Substances 0.000 title 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 10
- 238000000034 method Methods 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 229910000510 noble metal Inorganic materials 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- -1 methoxy, benzyloxy Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- OFIPMSSTKFSADG-UHFFFAOYSA-N [Li]CC#N Chemical compound [Li]CC#N OFIPMSSTKFSADG-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
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- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
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- C07C205/33—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups or etherified hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 다음 일반식(Ⅱ)의 화합물을 반응 불활성 용매 존재하, -60 내지 -80℃의 온도에서 일반식 LiCH2Q1의 리티오아세트산 에스테르 또는 리티오아세토니트릴과 반응시켜 다음 일반식(B)의 중간체 화합물을 형성하고, 이어서 (a) 이 중간체를 귀금속 촉매 존재하의 수소 대기하에서 가수소분해하거나, (b) 상술한 중간체를 탈수시키고 생성된 불포화 화합물을 수소화함을 특징으로 하여 다음 일반식(A)의 화합물을 제조하는 방법.상기식에서, M은 CH 또는 N이며; t는 1 또는 2이고; Q1은 COOR4[여기에서, R4는 H, (C1내지 C4) 알킬 또는 벤질이다]이며; R15는 H, (C1내지 C4)알킬 또는 벤질이고; M이 N이면, R16및 R17은 각각 수소이거나 또는 함께 카보닐 산소원자를 형성하며; M이 CH이면, R16및 R17은 각각 수소이고; Z1은 OH, 벤질옥시, (C1내지 C13)알콕시, (C5내지 C13)알킬, (C5내지 C13)알콕시알킬, (C8내지 C13)피리딜알킬, (C8내지 C13)-피리딜알콕시, (C8내지 C13)피리딜알콕시알킬, (C9내지 C14)페닐알킬, (C9내지 C14)-펜옥시알킬), (C9내지 C14)페닐알콕시 또는 (C9내지 C14)페닐알콕시알킬이다.
- 다음 일반식(Ⅷ)의 화합물을 탈수 조건하에서 폐환시킴을 특징으로 하여, 다음 일반식(Ⅸ)의 화합물을 제조하는 방법.상기식에서, M, t, R15및 Z1은 제1항에서 정의한 바와 같다.
- (a) 다음 일반식(D) 또는 (E)의 화합물을 반응 불활성 용매 및 금속하이드라이드나 귀금속촉매 존재하의 수소중에서 선택된 환원재 존재하에서 환원시키거나, 또는 (b) 다음 일반식(F)의 화합물을 리튬금속 및 무수 액체 암모니아로 환원시킴을 특징으로 하여, 다음 일반식(C)의 화합물을 제조하는 방법.상기식에서, M, t, Z1, R16및 R17은 제1항에서 정의한 바와 같으며, R1은 H 또는 아세틸이고; R4는 H, (C1내지 C4)알킬 또는 벤질이다.
- 제1항에 있어서, Q1이 COOR4이며, R4가 메틸 또는 에틸이고, R15가 메틸 또는 벤질이며, R16및 R17은 각각 수소이고, Z1은 메톡시, 벤질옥시, (C5내지 C13)알킬, (C5내지 C13)-알콕시, (C5내지 C1)-알콕시알킬, (C5내지 C13)-페닐알킬 또는 (C9내지 C14)페닐알콕시인 방법.
- 제1항 또는 3항에 있어서, 상술한 귀금속 촉매가 니켈, 팔라듐, 백금 또는 로듐인 방법.
- 제1항의 (b)에 있어서, 상술한 탈수반응을 메탄설폰산과 반응시키거나 플로리실 존재하, 60 내지 100℃에서 가열하여 수행하는 방법.
- 제2항에 있어서, 상술한 폐환 반응을 0°내지 100℃의 온도에서 아세트산/아세트산 무수물의 혼합물 또는 트리플루오로아세트산/트리플루오로아세트산 무수물의 혼합물 존재하에 수행하는 방법.
- 제1항, 2항 또는 3항중의 어느 하나에 있어서, Z1이 다음 일반식의 기인 방법.상기식에서, R13및 R14중의 하나는 H이고, 다른 하나는 CH3이다.
- 제8항에 있어서, R13이 H이고, R14가 CH3인 방법.
- 제3항의 (a)에 있어서, R4가 CH3또는 C2H5이고, 상술한 용매가 테트라하이드로푸란이며, 상술한 환원제는 리튬 알루미늄 하이드라이드인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US358569 | 1982-03-16 | ||
| US06/358,569 US4476131A (en) | 1982-03-16 | 1982-03-16 | Substituted hexahydropyrrolo[1,2-a]-quinolines, hexahydro-1H-pyrido[1,2-a]-q |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840004111A true KR840004111A (ko) | 1984-10-06 |
| KR870001126B1 KR870001126B1 (ko) | 1987-06-09 |
Family
ID=23410189
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830001021A KR870001126B1 (ko) | 1982-03-16 | 1983-03-15 | 치환된 헥사하이드로피롤로 [1,2-a]-퀴놀린 및 헥사하이드로-1H-피리도 [1,2-a]-퀴놀린의 제조방법 |
| KR1019860009393A KR880002412B1 (ko) | 1982-03-16 | 1986-11-07 | 치환된 헥사하이드로벤조 [e]인덴 및 옥타하이드로페난트렌의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860009393A KR880002412B1 (ko) | 1982-03-16 | 1986-11-07 | 치환된 헥사하이드로벤조 [e]인덴 및 옥타하이드로페난트렌의 제조방법 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4476131A (ko) |
| EP (1) | EP0090516B1 (ko) |
| JP (2) | JPS58170724A (ko) |
| KR (2) | KR870001126B1 (ko) |
| AR (1) | AR240936A1 (ko) |
| AT (1) | ATE35544T1 (ko) |
| AU (1) | AU543215B2 (ko) |
| CA (1) | CA1254567A (ko) |
| CS (1) | CS249126B2 (ko) |
| DD (2) | DD219765A5 (ko) |
| DE (1) | DE3377280D1 (ko) |
| DK (1) | DK85183A (ko) |
| ES (2) | ES520630A0 (ko) |
| FI (1) | FI76334C (ko) |
| GR (1) | GR77127B (ko) |
| HU (1) | HU189906B (ko) |
| IE (1) | IE54897B1 (ko) |
| IL (1) | IL68131A (ko) |
| NO (1) | NO162385B (ko) |
| NZ (1) | NZ203577A (ko) |
| PH (1) | PH19998A (ko) |
| PL (2) | PL141501B1 (ko) |
| PT (1) | PT76390B (ko) |
| RO (2) | RO88221B (ko) |
| SU (1) | SU1355130A3 (ko) |
| YU (2) | YU44736B (ko) |
| ZA (1) | ZA831781B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4576964A (en) * | 1982-03-16 | 1986-03-18 | Pfizer Inc. | Substituted hexahydrobenzo[e]indene and octahydrophenanthrene CNS agents and pharmaceutical compositions thereof |
| US4670562A (en) * | 1985-03-13 | 1987-06-02 | Hoechst-Roussel Pharmaceuticals Inc. | Dihydropyrrolo[1,2-b]isoquinolinedione oximes |
| US5629345A (en) * | 1993-07-23 | 1997-05-13 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| US5965620A (en) * | 1993-07-23 | 1999-10-12 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| CA2187257A1 (en) * | 1995-10-12 | 1997-04-13 | Enrique Luis Michelotti | Aryl-substituted cycloalkanes and cycloalkenes and herbicidal use thereof |
| CN1075498C (zh) * | 1997-05-08 | 2001-11-28 | 车庆明 | 一种查尔酮c甙和它的用途 |
| US6316734B1 (en) | 2000-03-07 | 2001-11-13 | 3M Innovative Properties Company | Flexible circuits with static discharge protection and process for manufacture |
| ITGE20080051A1 (it) | 2008-06-04 | 2009-12-05 | Matteucci Francesco | Metodo per la realizzazione di cavi diamantati rinforzati per il taglio di strutture e materiali in acciaio,calcestruzzo,acciaio e calcestruzzo,materiali litoidi o simili e cavo diamantato rinforzato ottenuto mediante tale metodo. |
| CN112778241A (zh) * | 2021-03-09 | 2021-05-11 | 中国科学院兰州化学物理研究所 | 一种四氢呋喃乙酸及其酯类化合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3045020A (en) * | 1962-07-17 | x xcooa | ||
| FR1490023A (fr) * | 1965-08-17 | 1967-07-28 | Sandoz Sa | Dérivés de l'isoquinoléine et leur préparation |
| US4260764A (en) * | 1976-12-22 | 1981-04-07 | Pfizer Inc. | 9-Hydroxyoctahydrobenzo [C] quinolines and intermediates therefor |
| US4188495A (en) * | 1977-11-14 | 1980-02-12 | Pfizer Inc. | 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor |
-
1982
- 1982-03-16 US US06/358,569 patent/US4476131A/en not_active Expired - Fee Related
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1983
- 1983-02-24 DK DK85183A patent/DK85183A/da not_active Application Discontinuation
- 1983-03-08 DE DE8383301224T patent/DE3377280D1/de not_active Expired
- 1983-03-08 AT AT83301224T patent/ATE35544T1/de not_active IP Right Cessation
- 1983-03-08 EP EP83301224A patent/EP0090516B1/en not_active Expired
- 1983-03-11 PL PL1983240989A patent/PL141501B1/pl unknown
- 1983-03-11 PL PL1983245846A patent/PL141640B1/pl unknown
- 1983-03-14 PH PH28641A patent/PH19998A/en unknown
- 1983-03-14 CA CA000423530A patent/CA1254567A/en not_active Expired
- 1983-03-14 DD DD83265108A patent/DD219765A5/de not_active IP Right Cessation
- 1983-03-14 DD DD83248795A patent/DD210270A5/de not_active IP Right Cessation
- 1983-03-14 YU YU606/83A patent/YU44736B/xx unknown
- 1983-03-15 RO RO114407A patent/RO88221B/ro unknown
- 1983-03-15 ZA ZA831781A patent/ZA831781B/xx unknown
- 1983-03-15 NZ NZ203577A patent/NZ203577A/en unknown
- 1983-03-15 HU HU842146A patent/HU189906B/hu not_active IP Right Cessation
- 1983-03-15 IE IE559/83A patent/IE54897B1/en unknown
- 1983-03-15 ES ES520630A patent/ES520630A0/es active Granted
- 1983-03-15 FI FI830857A patent/FI76334C/fi not_active IP Right Cessation
- 1983-03-15 PT PT76390A patent/PT76390B/pt unknown
- 1983-03-15 NO NO830900A patent/NO162385B/no unknown
- 1983-03-15 KR KR1019830001021A patent/KR870001126B1/ko not_active IP Right Cessation
- 1983-03-15 IL IL68131A patent/IL68131A/xx unknown
- 1983-03-15 AU AU12448/83A patent/AU543215B2/en not_active Ceased
- 1983-03-15 RO RO110332A patent/RO85382B/ro unknown
- 1983-03-15 GR GR70801A patent/GR77127B/el unknown
- 1983-03-16 CS CS831822A patent/CS249126B2/cs unknown
- 1983-03-16 JP JP58042538A patent/JPS58170724A/ja active Pending
- 1983-11-07 ES ES527075A patent/ES8504097A1/es not_active Expired
- 1983-11-28 SU SU833665902A patent/SU1355130A3/ru active
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1985
- 1985-03-11 AR AR299708A patent/AR240936A1/es active
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1986
- 1986-11-07 KR KR1019860009393A patent/KR880002412B1/ko not_active IP Right Cessation
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1987
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