KR880009946A - 테트라졸 화합물의 제조방법과 중간물질 - Google Patents
테트라졸 화합물의 제조방법과 중간물질 Download PDFInfo
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- KR880009946A KR880009946A KR1019880001915A KR880001915A KR880009946A KR 880009946 A KR880009946 A KR 880009946A KR 1019880001915 A KR1019880001915 A KR 1019880001915A KR 880001915 A KR880001915 A KR 880001915A KR 880009946 A KR880009946 A KR 880009946A
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- 238000000034 method Methods 0.000 title claims 6
- -1 tetrazole compound Chemical class 0.000 title claims 6
- 150000001875 compounds Chemical class 0.000 claims 57
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 239000011737 fluorine Substances 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000001246 bromo group Chemical group Br* 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 229910052740 iodine Chemical group 0.000 claims 3
- 239000011630 iodine Chemical group 0.000 claims 3
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 claims 3
- UMMDYIPYZBXCET-UHFFFAOYSA-N 5-[1,1-bis(4-fluorophenyl)prop-1-en-2-yl]-1-methyltetrazole Chemical compound N=1N=NN(C)C=1C(C)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 UMMDYIPYZBXCET-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 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
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- AHVNNBPDNBNCQO-UHFFFAOYSA-N 5-(2,2-diphenylethenyl)-1-methyltetrazole Chemical compound CN1N=NN=C1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 AHVNNBPDNBNCQO-UHFFFAOYSA-N 0.000 claims 1
- KJLDTARVSUXSKY-UHFFFAOYSA-N 5-[2,2-bis(2,4-dimethylphenyl)ethenyl]-1-methyltetrazole Chemical compound CC1=CC(C)=CC=C1C(C=1C(=CC(C)=CC=1)C)=CC1=NN=NN1C KJLDTARVSUXSKY-UHFFFAOYSA-N 0.000 claims 1
- IAMSEVFTBWWFBT-UHFFFAOYSA-N 5-[2,2-bis(2-fluoro-4-methylphenyl)ethenyl]-1-methyltetrazole Chemical compound FC1=CC(C)=CC=C1C(C=1C(=CC(C)=CC=1)F)=CC1=NN=NN1C IAMSEVFTBWWFBT-UHFFFAOYSA-N 0.000 claims 1
- XAVQJCJSXRLWHV-UHFFFAOYSA-N 5-[2,2-bis(4-fluoro-2-methylphenyl)ethenyl]-1-methyltetrazole Chemical compound CC1=CC(F)=CC=C1C(C=1C(=CC(F)=CC=1)C)=CC1=NN=NN1C XAVQJCJSXRLWHV-UHFFFAOYSA-N 0.000 claims 1
- PIMRADBFFIVGQX-UHFFFAOYSA-N 5-[2,2-bis(4-fluoro-3-methylphenyl)ethenyl]-1-methyltetrazole Chemical compound C1=C(F)C(C)=CC(C(=CC=2N(N=NN=2)C)C=2C=C(C)C(F)=CC=2)=C1 PIMRADBFFIVGQX-UHFFFAOYSA-N 0.000 claims 1
- JBMMOXNLHYKUEG-UHFFFAOYSA-N 5-[2,2-bis(4-fluorophenyl)ethenyl]-1-methyltetrazole Chemical compound CN1N=NN=C1C=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JBMMOXNLHYKUEG-UHFFFAOYSA-N 0.000 claims 1
- BTWVVUCIAJQOCB-UHFFFAOYSA-N 5-[2,2-bis(4-methoxyphenyl)ethenyl]-1-methyltetrazole Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)=CC1=NN=NN1C BTWVVUCIAJQOCB-UHFFFAOYSA-N 0.000 claims 1
- KNNSUKWBFZBAOW-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)-2-phenylethenyl]-1-methyltetrazole Chemical compound CN1N=NN=C1C=C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 KNNSUKWBFZBAOW-UHFFFAOYSA-N 0.000 claims 1
- ORZWCZCPJQGKQA-UHFFFAOYSA-N 5-[3-bromo-1,1-bis(4-fluorophenyl)prop-1-en-2-yl]-1-methyltetrazole Chemical compound CN1N=NN=C1C(CBr)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ORZWCZCPJQGKQA-UHFFFAOYSA-N 0.000 claims 1
- WYXQDGGJZMWJOX-UHFFFAOYSA-N 5-ethyl-1-methyltetrazole Chemical compound CCC1=NN=NN1C WYXQDGGJZMWJOX-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- OAAKZKGKPMPJIF-UHFFFAOYSA-N [Cl].[I] Chemical group [Cl].[I] OAAKZKGKPMPJIF-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 claims 1
- 150000008366 benzophenones Chemical class 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- NKSZZFWSGZJPEX-UHFFFAOYSA-N ethyl 3,3-bis(4-fluorophenyl)-2-(1-methyltetrazol-5-yl)prop-2-enoate Chemical compound N=1N=NN(C)C=1C(C(=O)OCC)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NKSZZFWSGZJPEX-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (38)
- 하기식의 화합물.상기식에서 R1와 R4는 각각 독립적으로 수소, 할로겐, C1-4알콕시 또는 트리플루오로메틸, R2,R3,R5와 R6는 각각 독립적으로 수소, 할로겐, C1-4 알콕시, B는 수소, C1-6 알콕시카르보닐, CH2Y 또는 CH2Z；Y는 수소, 히드록시 또는 X；Z는또는X; X는 브롬, 염소 또는 요오드；R10는 C1-4알킬 R11는 페닐로서 치환되지 않았거나 하나 또는 두 개의 C1-4또는 염소치환체로 치환됨.
- 제1항에 있어서, B가 수소인 화합물.
- 제2항에 있어서, R1,R2,R3,R4,R5와 R6는 각각 수소, 불소, 메틸 또는 메톡시에서 선택된 화합물.
- 제1항에 있어서, B가 C1-6알콕시카르보닐인 화합물.
- 제4항에 있어서, R1,R2,R3,R4,R5와 R6는 각각 수소, 불소, 메틸 또는 메톡시에서 선택된 화합물.
- 제1항에 있어서, 하기식의 화합물.상기식에서 R1와 R4는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸, R2,R3,R5와 R6는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 Y는 수소, 히드록시 또는 X；X는 브롬, 염소 또는 요오드.
- 제6항에 있어서, Y가 수소인 화합물.
- 제7항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시에서 선택된 화합물.
- 제6항에 있어서, Y가 히드록시인 화합물.
- 제9항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시에서 선택된 화합물.
- 제6항에 있어서, Y가 X이고 X는 브롬인 화합물.
- 제11항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시에서 선택된 화합물.
- 제1항에 있어서, 하기식의 화합물.상기식에서 R1과 R4는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸；R2,R3,R5와 R6은 각각 수소, 할로겐, C1-4알킬, C1-4알콕시；Z는또는 ；R10은 C1-4알킬；R11은 페닐로서 치환되지 않았거나 하나 또는 2개의 C1-4알킬 또는 염소치환체로 치환됨.
- 제13항에 있어서, Z가 트리페닐포스포늄 브로마이드인 화합물.
- 제14항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시에서 선택된 화합물.
- 제13항에 있어서, Z가 디메틸 포스포네이트인 화합물.
- 제16항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시에서 선택된 화합물.
- 제1항에 있어서, 1,1-비스(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)-1-프로펜인 화합물.
- 제1항에 있어서, 3,3-비스(4-플루오로페닐)-1-브로모-2-(1-메틸-1H-테트라졸-5-일)-2-프로펜인 화합물.
- 제1항에 있어서, 3,3-비스(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)2-프로펜인 화합물.
- 제1항에 있어서, [1,1-비스(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)-1-테트라졸-5-일)-1-프로펜-3-일]트리페닐포스포늄 브로마이드인 화합물.
- 제1항에 있어서, 1,1-비스(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 1,1-비스(2,4-디메틸페닐)-2-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 1,1-비스(4-플루오로-3-메틸페닐)-2-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 1,1-비스(4-플루오로-2-메틸페닐)-2-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 1,1-비스(2-플루오로-4-메틸페닐)-2-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 에틸 3,3-비스(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)2-프로페노에이트인 화합물.
- 제1항에 있어서, 1-(4-플루오로페닐)-2-(1-메틸-1H-테트라졸-5-일)-1-페닐에텐인 화합물.
- 제1항에 있어서, 2,2-디페닐-1-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 2,2-비스(4-메톡시페닐)-1-(1-메틸-1H-테트라졸-5-일)에텐인 화합물.
- 제1항에 있어서, 디메틸[3,3-비스(4-플루오로페닐)-2-(2-메틸-1H-테트라졸-5-일)-2-프로펜-1-일]포스포네이트인 화합물.
- (a) 하기식(V)의 화합물을 5-에틸-1-메틸-1H-테트라졸과 반응시켜 하기식(VIIa)의 화합물을 제조하고 (b) 식(VIIa)의 알콜을 탈수하여 하기식(Id)의 화합물을 제조하고 (c) 하기식(Id)의 올레핀을 할로겐화하여 하기식(Ie)의 화합물을 제조하고 (d) 하기식(Ie)의 화합물을 P(OR10)3또는 P(R11)3과 반응시키는 것으로 구성된 하기식(I) 화합물의 제조방법.상기식에서 R1는 R4는 각각 독립적으로 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸；R2,R3,R5와 R6는 각각 독립적으로 수소, 할로겐 C1-4알킬, C1-4알콕시；Z는또는；R10는 C1-4알킬 R11는페닐로서 치환되지 않았거나 하나 또는 두 개의 C1-4알킬 또는 C1-4알킬 또는 염소 치환체로 치환됨. X는 브롬, 염소 요오드.
- 제32항에 있어서, R1,R2,R3,R4,R5와 R6가 각각 수소, 불소, 메틸과 메톡시로 구성된 군에서 선택된 방법.
- 제33항에 있어서, Z가 트리페닐포스포늄 브로마이드인 방법.
- 제33항에 있어서, Z가 디메틸 포스포네이트인 방법.
- (a) 하기식(V)의 치환된 또는 비치환된 벤조 페논을 하기식(VI)의 화합물과 반응시켜 식(VII)의 화합물을 산출한 뒤 (b) 상기 단계(a)의 생성물을 탈수하여 R8이 수소, C1-6알콕시 카르보닐 또는 메틸인 식(I′)의 화합물을 산출하고, (c) 상기 단계(b)의 R8이 메틸인 생성물을 촉매의 존재하에서 N-할리디 석신이미드와 반응시켜 R8이 메틸 할라이드인 식(I′)의 화합물을 산출하고 (d) 상기 단계(b)의 R8이 C2알콕시카르보닐인 생성물을 비환원성 용매내에서 환원제와 반응시켜 R8이 CH2OH인 식(I′)의 화합물을 산출하는 것으로 구성된 하기식I′)화합물의 제조방법.상기식에서 R1과 R4는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸；R2,R3,R5와 R6는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시；B는 수소, C1-6알콕시카르보닐 또는 CH2Y Y는 수소, 히드록시 또는 X；X는 브롬, 염소 또는 요오드.
- (a) 하기식(Ie)의 화합물을 트리페닐 포스파인과 반응시켜 하기식 (If)의 포스포늄염을 제조하거나 포스파이트와 반응시켜 하기식(Ig)의 화합물을 제조하고 (b) 단계(a)의 생성물중 하나를 강염기가 존재하는 불활성 유기 용매내에서 하기식(XI)의 화합물과 반응시키거나 (c) 단계(b)의 생성물을 소량의 유기산이 존재하는 불활성 유기 용매내에서 탈실릴화제와 반응시켜 탈실릴화하여 R7이 가수분해가 용이한 에스테르인 식(IIa)의 화합물을 산출하고 (d)는 유기 용매내에서 염기 가수분해에 의하여 R7에스테르기를 분리하여 R7이 O-M+,M+이 양이온인 식(IIa)의 화합물을 산출하고 (e) 단계(d)의 생성물을 산성화하여 R7이 수소인 식(IIa)의 화합물을 산출하고 (f) 단계(e)의 생성물을 불활성 유기 용매내에서 카르보디이미드로서 카르복실라디칼을 활성화시켜 고리화함으로서 식(IIb)의 화합물을 제조하는 것으로 구성된 식(IIa) 또는 (IIb) 화합물의 제조방법.상기식에서 R1과 R4는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸；R2,R3,R5와 R6는 각각 수소, 할로겐, C1-4알킬 또는 C1-4알콕시 n은 1 R7은 수소, 가수분해가 가능한 에스테르 또는 양이온으로서 비독성이며 약학적으로 허용 가능한 염을 형성할 수 있다. R9는 가수분해가 가능한 에스테르 R10은 C1-4알킬 R11은 비치환된 또는 치환된 페닐, R12는 t-부틸디페닐 실릴.
- (a) 하기식(V)의 화합물을 하기식(VI) 화합물의 음이온과 반응시켜 하기식(VII)의 화합물을 생성하고 (b) 단계 (a)의 생성물을 탈수하여 식(IV)의 화합물을 산출하고 (c) 불활성 유기 용매내에서 생성된 R8이 수소인 식(IV)의 화합물의 음이온을 강염기로 처리하거나 (C′) R8이 메틸인 식(IV)의 화합물을 촉매의 존재하에서 N-할리디석신이미드와 반응시킨 뒤 산출된 생성물을 2-니트로프로판과 반응시켜 하기식(III)의 화합물을 산출하는 것으로 구성된 하기식(III)의 화합물의 제조방법.상기식에서 R1과 R4는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 또는 트리플루오로메틸, R2,R3,R5와 R6는 각각 수소, 할로겐, C1-4알킬, C1-4알콕시 R8은 수소, C1-6알콕시카르보닐 또는 메틸.※참고사항:최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1855887A | 1987-02-25 | 1987-02-25 | |
| JP018,558 | 1987-02-25 | ||
| US018558 | 1987-02-25 | ||
| US151512 | 1988-02-18 | ||
| US07/151,512 US4898949A (en) | 1987-02-25 | 1988-02-18 | Intermediates for the preparation of antihypercholesterolemic tetrazole compounds |
| JP151,512 | 1988-02-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR880009946A true KR880009946A (ko) | 1988-10-06 |
| KR960007167B1 KR960007167B1 (ko) | 1996-05-29 |
Family
ID=26691250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880001915A KR960007167B1 (ko) | 1987-02-25 | 1988-02-24 | 과콜레스테롤혈증 억제성 테트라졸 화합물의 제조방법과 중간물질 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4898949A (ko) |
| JP (1) | JP2603284B2 (ko) |
| KR (1) | KR960007167B1 (ko) |
| CN (1) | CN1030077C (ko) |
| AT (1) | AT395588B (ko) |
| AU (1) | AU610562B2 (ko) |
| BE (1) | BE1002115A3 (ko) |
| CA (1) | CA1328269C (ko) |
| CH (1) | CH678182A5 (ko) |
| DE (1) | DE3805789C2 (ko) |
| DK (2) | DK97388A (ko) |
| ES (1) | ES2009547A6 (ko) |
| FI (1) | FI96600C (ko) |
| FR (1) | FR2611201B1 (ko) |
| GB (1) | GB2202845B (ko) |
| GR (1) | GR1000473B (ko) |
| HU (3) | HU201534B (ko) |
| IE (1) | IE61608B1 (ko) |
| IT (1) | IT1216752B (ko) |
| LU (1) | LU87143A1 (ko) |
| MY (1) | MY102290A (ko) |
| NL (1) | NL8800468A (ko) |
| NO (1) | NO178432C (ko) |
| NZ (1) | NZ223621A (ko) |
| PT (1) | PT86821B (ko) |
| SE (3) | SE504553C2 (ko) |
| YU (1) | YU46781B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870187A (en) * | 1988-08-23 | 1989-09-26 | Bristol-Myers Company | Antihypercholesterolemic tetrazol-1-yl compounds |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5260325A (en) * | 1991-08-19 | 1993-11-09 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking tertiary amides |
| CA2137049A1 (en) * | 1993-12-15 | 1995-06-16 | John K. Thottathil | Amino acid salts of and methods for preparing antihypercholesterolemic tetrazole compounds |
| KR100681366B1 (ko) * | 1997-12-19 | 2007-02-12 | 워너-램버트 익스포트 리미티드 | 1,3-디올의 합성방법 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160100A (en) * | 1973-03-23 | 1979-07-03 | American Home Products Corporation | Oxamic acid derivatives |
| US4013647A (en) * | 1976-03-23 | 1977-03-22 | American Home Products Corporation | Morpholine containing tetrazole-5-carboxamide derivatives |
| JPS53147073A (en) * | 1977-05-24 | 1978-12-21 | Sankyo Co Ltd | Mevalonolactone derivatives |
| NZ194557A (en) * | 1979-08-17 | 1984-09-28 | Merck & Co Inc | Substituted pyranone derivatives;dihydroxy acids therefrom;pharmaceutical compositions |
| US4567289A (en) * | 1979-08-17 | 1986-01-28 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
| US4375475A (en) * | 1979-08-17 | 1983-03-01 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
| EP0068038B1 (en) * | 1981-06-29 | 1985-09-25 | Merck & Co. Inc. | (+)-(4r,6s)-(e)-6-(2-(4'-fluoro-3,3',5-trimethyl-(1,1'-biphenyl)-2-yl)ethenyl)-3,4,5,6-tetrahydro-4-hydroxy-2h-pyran-2-one, a process for preparing and a pharmaceutical composition containing the same |
| AU570021B2 (en) * | 1982-11-22 | 1988-03-03 | Novartis Ag | Analogs of mevalolactone |
| US4739073A (en) * | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| PT77996B (en) * | 1983-01-24 | 1986-05-30 | Sandoz Sa | Process of the preparations of mevalonelactone analogs and derivatives thereof and of pharmaceutical compositions containing them |
| US5105017A (en) * | 1983-07-18 | 1992-04-14 | Eli Lilly And Company | Leukotriene antagonist intermediates |
| CA1327360C (en) * | 1983-11-14 | 1994-03-01 | William F. Hoffman | Oxo-analogs of mevinolin-like antihypercholesterolemic agents |
| US4613610A (en) * | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
| JPS61502467A (ja) * | 1984-06-22 | 1986-10-30 | サンド・アクチエンゲゼルシヤフト | メバロノラクトンのピラゾ−ル同族体およびその誘導体、それらの製造方法ならびに用途 |
| US4668794A (en) * | 1985-05-22 | 1987-05-26 | Sandoz Pharm. Corp. | Intermediate imidazole acrolein analogs |
| US4621099A (en) * | 1985-09-23 | 1986-11-04 | Usv Pharmaceutical Corporation | Polyene compounds useful in the treatment of allergic responses |
| US4681893A (en) * | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
| US4678806A (en) * | 1986-09-02 | 1987-07-07 | Merck & Co., Inc. | Prodrugs of antihypercholesterolemic compounds |
| AU601264B2 (en) * | 1987-02-25 | 1990-09-06 | Bristol-Myers Squibb Company | Antihypercholesterolemic tetrazole compounds |
-
1988
- 1988-02-18 US US07/151,512 patent/US4898949A/en not_active Expired - Lifetime
- 1988-02-24 AT AT0046088A patent/AT395588B/de not_active IP Right Cessation
- 1988-02-24 JP JP63041828A patent/JP2603284B2/ja not_active Expired - Fee Related
- 1988-02-24 ES ES8800533A patent/ES2009547A6/es not_active Expired
- 1988-02-24 FR FR888802212A patent/FR2611201B1/fr not_active Expired - Fee Related
- 1988-02-24 AU AU12132/88A patent/AU610562B2/en not_active Ceased
- 1988-02-24 IE IE50288A patent/IE61608B1/en not_active IP Right Cessation
- 1988-02-24 IT IT8819526A patent/IT1216752B/it active
- 1988-02-24 CH CH691/88A patent/CH678182A5/de not_active IP Right Cessation
- 1988-02-24 GR GR880100100A patent/GR1000473B/el not_active IP Right Cessation
- 1988-02-24 KR KR1019880001915A patent/KR960007167B1/ko not_active IP Right Cessation
- 1988-02-24 NL NL8800468A patent/NL8800468A/nl not_active Application Discontinuation
- 1988-02-24 HU HU895133A patent/HU201534B/hu not_active IP Right Cessation
- 1988-02-24 CA CA000559671A patent/CA1328269C/en not_active Expired - Fee Related
- 1988-02-24 GB GB8804281A patent/GB2202845B/en not_active Expired - Fee Related
- 1988-02-24 DE DE3805789A patent/DE3805789C2/de not_active Expired - Fee Related
- 1988-02-24 MY MYPI88000180A patent/MY102290A/en unknown
- 1988-02-24 FI FI880868A patent/FI96600C/fi not_active IP Right Cessation
- 1988-02-24 HU HU895124A patent/HU201533B/hu not_active IP Right Cessation
- 1988-02-24 NO NO880802A patent/NO178432C/no not_active IP Right Cessation
- 1988-02-24 HU HU88885A patent/HU201532B/hu not_active IP Right Cessation
- 1988-02-24 DK DK097388A patent/DK97388A/da not_active Application Discontinuation
- 1988-02-24 SE SE8800637A patent/SE504553C2/sv not_active IP Right Cessation
- 1988-02-24 NZ NZ223621A patent/NZ223621A/en unknown
- 1988-02-24 PT PT86821A patent/PT86821B/pt not_active IP Right Cessation
- 1988-02-25 LU LU87143A patent/LU87143A1/fr unknown
- 1988-02-25 BE BE8800219A patent/BE1002115A3/fr not_active IP Right Cessation
- 1988-02-25 YU YU36488A patent/YU46781B/sh unknown
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1992
- 1992-10-20 CN CN92111551A patent/CN1030077C/zh not_active Expired - Fee Related
-
1993
- 1993-03-24 SE SE9300976A patent/SE503201C2/sv not_active IP Right Cessation
- 1993-03-24 SE SE9300977A patent/SE512485C2/sv not_active IP Right Cessation
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1997
- 1997-10-06 DK DK113897A patent/DK113897A/da not_active Application Discontinuation
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