KR900018088A - 피페리디닐, 피롤리디닐 및 피레라지닐 알킬페놀 에테르 유도체 - Google Patents
피페리디닐, 피롤리디닐 및 피레라지닐 알킬페놀 에테르 유도체 Download PDFInfo
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- KR900018088A KR900018088A KR1019900006908A KR900006908A KR900018088A KR 900018088 A KR900018088 A KR 900018088A KR 1019900006908 A KR1019900006908 A KR 1019900006908A KR 900006908 A KR900006908 A KR 900006908A KR 900018088 A KR900018088 A KR 900018088A
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- 150000002170 ethers Chemical class 0.000 title 1
- 125000003386 piperidinyl group Chemical group 0.000 title 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 239000012442 inert solvent Substances 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 230000000840 anti-viral effect Effects 0.000 claims 3
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 2
- -1 5-bromo-1 , 3,4-thiadiazol-2-yl Chemical group 0.000 claims 2
- 238000007126 N-alkylation reaction Methods 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000005283 haloketone group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
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Claims (10)
- 일반식(Ⅰ)의 화합물, 그 부가염 또는 입체 이성체위의 일반식에서, Het는Y는 O 또는 S이고, Y'은 S또는 SO2이고, R5및 R6은 각각 수소, 트리플루오로메틸, 할로, 아미노, C1-4알킬옥시, C1-4알킬옥시카르보닐 또는 아릴이고, m 및 n은 가가 1 내지 4의 정수이며, m 및 n의 화는 3,4 또는 5이고, X는 N 또는 CH이고, Alk는 C1-4알칸디일이고 R1및 R2는 각각 수소, C1-4알킬 또는 할로이고, R3는 수소, 할로시아노, C1-4알킬옥시, 아릴 또는 -COOR4이고, R4는 수소, C1-4알킬, 아릴, C1-4알킬, C3-6시클로알킬, C1-4알킬, C3-5알케닐, C3-5알키닐 또는 C1-4알킬옥시, C1-4알킬 이거나 R3은R7및 R8은 각각 수소, C1-4알킬, 아릴 또는 아릴C1-4알킬이고, 아릴은 페닐이기, 할로, C1-4알킬, 트리플루오로메틸 C1-4알킬옥시 및 히드록시로 부터 선택한 1 또는 2의 기로 치환된 페닐이다.
- 제1항에 있어서, n은 1,2 또는 3이고, Het가 식(a)의 기이고, 상기 식중 R5는 수소 또는 할로이고, R6은 수소, C1-4알킬, 옥시카르보닐 또는 아릴이거나, 식(b)의 기이고, 상기 식중 R5는 수소 C1-4알킬, 할로아미노 또는 아릴이거나, 식(c)의 기이고, 상기 식중 R5는 수소C1-4알킬 또는 아릴이거나, 식(d) 또는 (e)의 기인 일반식(Ⅰ)의 화합물, 그 부가염 또는 입체이성체.
- 제2항에 있어서, R1및 R2가 각각 수소 또는 할로이고, R3이 -COOR4의 기이고, 상기식중 R4는 C1-4알킬, C3-5알케닐, C3-5알키닐 또는 C1-4알킬옥시, C1-4알킬 이거나, R3이 식(f), (g), (h), (i) 또는 (j)의 기이고, 상기 식중 R7및 R8이 각각 수소 또는 C1-4알킬인 일반식(Ⅰ)의 화합물, 그 부가염 또는 입체이성체.
- 제3항에 있어서, Het가 식(a)의 기이고, 상기식중 R5가 수소이고, R6이 수소 또는 C1-4알킬옥시카르보닐이거나, 식(b)의 기이고, 상기 식중 R5가 수소, C1-4알킬, 할로 아릴아릴이거나, 식(d)의 기이고, 상기 식중 R1는 SO2이거나 식(e)의 기이고, R1및 R2가 모두 수소이고, R3이 C1-4알킬옥시카르보닐 또는 1,2,4-옥사디아졸-5-일[식(ⅰ)]이고, 상기 식중 R7이 C1-4알킬인 일반식(Ⅰ)의 화합물, 그 부가염 또는 입체이성체.
- 제4항에 있어서, n 및 m이 모두 2이고 Het가 식(b)의 기(식중 R5는 수소, 메틸, 에틸, 클로로, 브로모 또는 에틸이고 Y가 S)인 일반식(Ⅰ)의 화합물 그 부가염 또는 입체이성체,
- 제1항에 있어서, 화합물이 에틸 4-[2-[1-(5-메틸-1,3,4-티아디아졸-2-일)-4-피페리디닐]에톡시]벤조에이트, 에틸 4-[2-[1-(5-브로모-1,3,4-티아디아졸-2-일)-4-피페리디닐]에톡시]벤조에이트 또는 1-(5-브로모-1,3,4-티아디아졸-2-일)-4-[2-[4-(3-1,2,4-옥사디아졸-5-일)페녹시]-에틸]피페리딘 화합물, 그 부가염 또는 입체이성체.
- 온혈동물에 청구범위 제1항 내지 제6항중 어느 한항의 일반식(Ⅰ)의 화합물을 항비루스 효과량 국부 또는 전시투여하여, 비루스성장을 억제, 예방 또는 퇴치하는 방법.
- 청구범위 제1항 내지 제6항중 어느 한항의 일반식(Ⅰ)의 화합물을 유효성분으로 항비루스효과량 조성하고 불활성담체와 임의로 다른 부가제를 조성시킨 다음 부가제를 조성시킨 항비루스약제조성물.
- 제8항에 있어서, 시클로덱스트린 또는 그 유도체를 조성시킨 약제 조성물.
- a) 일반식(Ⅱ)의 아민을 일반식(Ⅲ)의 복소환과 불활성 용매중에서 N-알킬화 반응시키거나, b) 일반식(Ⅴ)의 페놀을 일반식(Ⅳ)의 화합물과 불활성용매중에서 0-알킬화 반응시키거나, c) 일반식(Ⅴ)의 페놀을 일반식(Ⅵ)의 알콕과 디에틸 아조디카르복시레이트 및 트리페닐포스핀 존재하에 무수 불활성용매중에서 0-알킬화반응시키거나, d) 일반식(Ⅵ)의 알콜을 일반식(Ⅶ)의 화합물과 불활성 용매중에서 0-알킬화 반응시키거나, e)일반식(Ⅷ)의 피피라진 아민을 일반식(Ⅸ)의 화합물과 불활성 용매중에서 반응시키거나, [일반식(Ⅰ-)의 화합물 생성]. f) 일반식(Ⅷ)의 피피라지 아민을 일반식(Ⅸ)의 화합물과 불활성용매중에서 환원성 N-알킬화 반응시키거나 [일반식(Ⅰ-)의 화합물 생성], g) 일반식(ⅩI)의 화합물을 일반식(XⅡ)의 아민가 불활성 용매중에서 폐환반응시키거나, [일반식(Ⅰ-)의 화합물을 생성]. h) 일반식(XⅢ)의 케톤을 일반식(XV)의 일리드와 불활성용매중에서 반응시키고 이어서 생성된 일반식(XVⅡ)의 화합물을 수소 및 촉매 존재하에 불활성 용매중에서 환원시키거나, [일반식(Ⅰ-)의 화합물 생성], i) 일반식(XⅣ)의 알레히드를 일반식(XⅥ)의 일리드와 불활성용매중에서 반응시키고, 이어서 생성된 일반식(XⅧ)의 화합물을 환원시키거나[일반식(Ⅰ-)의 화합물 생성], j) 일반식(XⅢ)의 케톤을 일반식(XⅨ) 유기금속화합물과 불활성용매중에서 반응시키고, 이어서 생성된 일반식(XX)의 화합물을 불활성 용매중에서 탈수 및 수소첨가반응시키거나, [일반식(Ⅰ-)의 화합물 생성],l)일반식(XXI)의 아실아미노케톤을 불화성용매중에서 탄수 페환반응(cyclodehydratinh)시키거나[일반식(Ⅰ-a-1)의 화합물 생성],m) 일반식(XXⅡ)의 티오우레아를 일반식(XXⅢ)의-할로케톤 또는 알데히드와 불활성용매중에서 반응시키거나, [일반식(Ⅰ-a-2)의 화합물 생성], n) 일반식(XXⅣ)의 디아실히드라지드를 탈수제로 불활성 용매중에서 탈수 페환 반응시키거나, [일반식(Ⅰ-b-1)의 화합물 생성],o) 일반식(XXⅣ)의 디아실히드라지를 5황화인으로 불활성 용매중에서 페환반응시키거나 [일반식(Ⅰ-a-1)의 화합물 생성], p) 일반식(XXⅥ-b-1:Y=O) 또는 (XXⅥ-b-2:Y=S)의 히드라지들 일반식 R3-C(OC1-4알킬)3의 오르트 에스테르와 불활성용매중에서 축합반응시키거나[일반식(Ⅰ-b-1:Y=O) 또는 (Ⅰ-b-1:Y=S)의 화합물 생성], q) 일반식(XXⅧ-c-1:Y=O) 또는 (XXⅧ-c-2:Y=S)의 화합물을 일반식(XXⅦ)의 아미독심가 불활성 용매중에서 반응시키거나, [일반식(Ⅰ-c-1:Y=O) 또는 (Ⅰ-c-1:Y=S)의 화합물 생성],r)일반식(XXⅨ)의 2-아미노(티오) 페놀을 일반식 할로와 불활성용매중에서 반응시키거나, [일반식(Ⅰ-e-1:Y=O) 또는 (Ⅰ-e-1:Y=S)의 화합물 생성], s) 일반식(XXⅨ)의 2-아미노(티오) 페놀을 일반식(XXXI)와 이미데이트와 불활성용매중에서 반응시키거나, [일반식(Ⅰ-e-1:Y=O) 또는 (Ⅰ-e-1:Y=S)의 화합물 생성], t) 일반식(Ⅰ-k)의 화합물 일반식(XXXⅡ)와 아미독심과 불활성용매중에서 반응시키거나, [일반식(Ⅰ-i)의 화합물 생성], u) 일반식(Ⅰ-i)의 화합물을 히드록실아민 또는 그 산부가염과 반응시키고, 이어서 생성된 아미독심을 일반식 HOOC-R7(XXⅢ)의 카르복시산과 불활성용매중에사 반응시키거나, [일반식(Ⅰ-j)의 화합물 생성]시켜, 일반식(Ⅰ)의 화합물, 그 부가염 또는 입체 이성체를 제조하는 방법.위의 일반식에서, Het는Y는 O 또는 S이고, Y'은 S또는 SO2이고, R5및 R6은 각각 수소, 트리플루오로메틸, 할로, 아미노, C1-4알킬옥시, C1-4알킬옥시카르보닐 또는 아릴이고, m 및 n은 가가 1 내지 4의 정수이며, m 및 n의 화는 3,4 또는 5이고, X는 N 또는 CH이고, Alk는 C1-4알칸디일이고 R1및 R2는 각각 수소, C1-4알킬 또는 할로이고, R3는 수소, 할로, 시아노, C1-4알킬옥시, 아릴 또는 -COOR4이고, R4는 수소, C1-4알킬, 아릴, C1-4알킬, C3-6시클로알킬, C1-4알킬, C3-5알케닐, C3-5알키닐 또는 C1-4알킬옥시, C1-4알킬 이거나 R3은R7및 R8은 각각 수소, C1-4알킬, 아릴 또는 아릴C1-4알킬이고, 아릴은 페닐이거나, 할로, C1-4알킬, 트리플루오로메틸 C1-4알킬옥시 및 히드록시로 부터 선택한 1 또는 2의 기로 치환된 페닐이고, W는 반응성 이탈기이고, O=Alk'는 H-Alk에서 한쌍의 수소가 산소원자로 치환된 것이고, R9및 R10는 아릴 또는 C1-6알킬이거나, R9는 알킬옥시이고, R10은 O이고, (R9)2R10P-Alk'는 H-Alk에서 한쌍의 수소원자가 (R9)2R10P로 치환된 것이고, (R9)2R10P-Alk'는 H-Alk에서 한쌍의 수소원자가 (R9)2R10P로 치환되고 메틸렌 하나가 빠진 것이고, M은 금속 원자이고, D는W1은 할로이고, R8은 수소 또는 C1-4알킬이고, R12는 수소 또는 C1-4알킬이다.※참고사항 : 최초출원내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35169789A | 1989-05-15 | 1989-05-15 | |
| US35169889A | 1989-05-15 | 1989-05-15 | |
| US7351697 | 1989-05-15 | ||
| US7351698 | 1989-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900018088A true KR900018088A (ko) | 1990-12-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900006908A KR900018088A (ko) | 1989-05-15 | 1990-05-15 | 피페리디닐, 피롤리디닐 및 피레라지닐 알킬페놀 에테르 유도체 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0398425B1 (ko) |
| JP (1) | JPH0347174A (ko) |
| KR (1) | KR900018088A (ko) |
| AT (1) | ATE102929T1 (ko) |
| AU (1) | AU628172B2 (ko) |
| CA (1) | CA2016742A1 (ko) |
| DE (1) | DE69007330T2 (ko) |
| DK (1) | DK0398425T3 (ko) |
| ES (1) | ES2053077T3 (ko) |
| IE (1) | IE63536B1 (ko) |
| IL (1) | IL94382A (ko) |
| NZ (1) | NZ233525A (ko) |
| PT (1) | PT94035B (ko) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| FR2658823B1 (fr) * | 1990-02-27 | 1992-04-30 | Adir | Nouveaux derives d'aminomethylpiperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent . |
| FR2675802B1 (fr) * | 1991-04-26 | 1993-12-24 | Rhone Poulenc Rorer Sa | Antiserotonines, leur preparation et les medicaments les contenant. |
| DE4136900C1 (ko) * | 1991-11-09 | 1993-07-29 | Schaper & Bruemmer Gmbh & Co Kg, 3320 Salzgitter, De | |
| JP3193560B2 (ja) * | 1993-04-16 | 2001-07-30 | 明治製菓株式会社 | 新規ベンゾオキサゾール誘導体 |
| DE69405535T2 (de) * | 1994-03-11 | 1998-04-02 | Agfa Gevaert Nv | Photographisches Material, das einen neuen Typ eines Hydrazides enthält |
| MX9709451A (es) * | 1995-06-06 | 1998-02-28 | Hoechst Marion Roussel Inc | Derivados de benzisoxazol e indazol como agentes antipsicoticos. |
| AUPQ105499A0 (en) | 1999-06-18 | 1999-07-08 | Biota Scientific Management Pty Ltd | Antiviral agents |
| AUPR213700A0 (en) | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
| EP1879885A1 (en) * | 2005-05-04 | 2008-01-23 | F. Hoffmann-Roche AG | Heterocyclic antiviral compounds |
| US8097610B2 (en) * | 2005-08-26 | 2012-01-17 | Shionogi & Co., Ltd. | Derivative having PPAR agonistic activity |
| CN102485717B (zh) * | 2010-12-06 | 2015-12-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 噻唑胺衍生物及其作为抗小rna病毒感染药物的用途 |
| US8981095B2 (en) | 2011-07-28 | 2015-03-17 | Mapi Pharma Ltd. | Intermediate compounds and process for the preparation of lurasidone and salts thereof |
| US10253021B2 (en) | 2015-12-22 | 2019-04-09 | Sumitomo Chemical Company, Limited | Method for producing benzoxazole compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4089965A (en) * | 1976-03-26 | 1978-05-16 | American Cyanamid Company | Thiazolylphenylguanidines as antirhinovirus agents |
| US4140785A (en) * | 1978-05-08 | 1979-02-20 | E. I. Du Pont De Nemours And Company | N-(benzothienopyrazol)amide antirhinoviral agents |
| US4590196A (en) * | 1984-08-23 | 1986-05-20 | Bristol-Myers Company | Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives |
| US4576943A (en) * | 1984-10-09 | 1986-03-18 | American Cyanamid Company | Pyrazolo[1,5-a]pyrimidines |
-
1990
- 1990-05-01 NZ NZ233525A patent/NZ233525A/xx unknown
- 1990-05-10 EP EP90201184A patent/EP0398425B1/en not_active Expired - Lifetime
- 1990-05-10 AT AT90201184T patent/ATE102929T1/de not_active IP Right Cessation
- 1990-05-10 AU AU54941/90A patent/AU628172B2/en not_active Ceased
- 1990-05-10 DK DK90201184.0T patent/DK0398425T3/da active
- 1990-05-10 DE DE69007330T patent/DE69007330T2/de not_active Expired - Fee Related
- 1990-05-10 ES ES90201184T patent/ES2053077T3/es not_active Expired - Lifetime
- 1990-05-14 IE IE172790A patent/IE63536B1/en not_active IP Right Cessation
- 1990-05-14 PT PT94035A patent/PT94035B/pt not_active IP Right Cessation
- 1990-05-14 CA CA002016742A patent/CA2016742A1/en not_active Abandoned
- 1990-05-14 IL IL9438290A patent/IL94382A/en not_active IP Right Cessation
- 1990-05-15 JP JP2125260A patent/JPH0347174A/ja active Pending
- 1990-05-15 KR KR1019900006908A patent/KR900018088A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PT94035A (pt) | 1991-01-08 |
| IE901727L (en) | 1990-11-15 |
| IL94382A (en) | 1994-11-11 |
| AU628172B2 (en) | 1992-09-10 |
| EP0398425A1 (en) | 1990-11-22 |
| PT94035B (pt) | 1996-11-29 |
| NZ233525A (en) | 1991-09-25 |
| DK0398425T3 (da) | 1994-04-05 |
| CA2016742A1 (en) | 1990-11-15 |
| ATE102929T1 (de) | 1994-04-15 |
| DE69007330T2 (de) | 1994-07-07 |
| AU5494190A (en) | 1990-11-15 |
| EP0398425B1 (en) | 1994-03-16 |
| DE69007330D1 (de) | 1994-04-21 |
| JPH0347174A (ja) | 1991-02-28 |
| IL94382A0 (en) | 1991-03-10 |
| IE63536B1 (en) | 1995-05-17 |
| ES2053077T3 (es) | 1994-07-16 |
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