KR840003628A - 피리딜화합물의 제조방법 - Google Patents
피리딜화합물의 제조방법 Download PDFInfo
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- KR840003628A KR840003628A KR1019830000440A KR830000440A KR840003628A KR 840003628 A KR840003628 A KR 840003628A KR 1019830000440 A KR1019830000440 A KR 1019830000440A KR 830000440 A KR830000440 A KR 830000440A KR 840003628 A KR840003628 A KR 840003628A
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- Prior art keywords
- compound
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- enyl
- pyrrolidino
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- 238000000034 method Methods 0.000 title claims 9
- -1 pyridyl compound Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000002148 esters Chemical class 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- QWPBWIRUYTZEFI-UHFFFAOYSA-N 2-pyridin-2-ylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=N1 QWPBWIRUYTZEFI-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
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- C07—ORGANIC CHEMISTRY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 다음식(Ⅵ)의 화합물 혹은 그 에스테르와 HNR2R3아민을 반응시키고, R1이(CH2)0이고 A와 B는 수소인 식(Ⅰ)의 화합물 제조시 다음식(Ⅶ)의 화합물과 C1-6알킬리튬 화합물과 반응시키고 이산화탄소로 처리하고, R1이 (CH2)aCH=CH(CH2)b이고, a는 인식(Ⅰ)의 화합물 제조시 다음식(Ⅶ)이 화합물과 COR6가 상술한산, 에스테르 혹은 아미드기인 측쇄 CH=CH(CH2)bCOR6의 부착에 알맞는 비티기시약과 반응시키고 카르복시기의 탈보호 처리하고, CA-CB가 이중 결합인 식(Ⅰ)의 화합물 제조시 식(Ⅰ)의 화합물 제조시 i)다음식(Ⅸ)의 화합물의 에스테르, 아미드 혹은 카르복실산염과 X와 R1에서 R4가 상술한 대로인 측쇄 =CH CH2NR2R3의 부착에 알맞는 비티그시약과 반응후 카르복시보호기의 탈보호화하고 ii)다음식 (Ⅹ)의 화합물 혹은 에스테르 혹은 그 아미드에서 R7OH의 제거 ⅲ)다음식(ⅩⅠ)의 화합물과 HNR2R3와 반응시키고, 이후식(Ⅰ)의 화합물을 공지기법으로 식(Ⅰ)의 타화합물로 전환시키는 단계로 구성되는 다음식(Ⅰ)의 화합물, 그 염, 에스테르 혹은 아미드를 제조하는 방법:상기식에서 R1은 C1-7가 지방족 탄화수소기 혹은 단일결합이고; R2와 R3는 동일하거나 서로 다른 것으로서 각기 수소, C1-4알킬 혹은 질소원자를 지니는 것으로서 질소원자를 지니는 4에서 6원소환을 지니는 헤테로시클릭환이고; R4는 수소, 할로겐, 히드록시, 시아노 C1-4아릴옥시, C1-4알콕시 혹은 1-3할로겐원자로 치환된 C1-4알킬이고; X는 N=혹은 -CH이고 A와 B는 수소원자 혹은 -CA-CB-는 -C=C-를 나타내며; L은 분리기이고; R5는 할로겐원자이고; R1은 수소 혹은 C1-4아실이고; R8은 C1-4아실옥시기임.
- 청구범위 1항에 있어서 다음식(Ⅱ)의 화합물, 그염, 에스테르 혹은 아미드를 제조하는 방법.상기식에서 R1에서 R4, X, A 및 B는 상기한 대로임.
- 청구범위 1 혹은 항2에 있어서 R1이 n이 0에서 7인 정수인(CH2)n이고 a와 b는 각기 0에서 5 이며 a와 b의 합은 5를 넘지 않는 (CH2)aCH=CH(CH2)b인 화합물의 제조방법.
- 청구범위 제1에서 3중의 하나의 항에서 다음식(Ⅲa) 혹은 (Ⅲb)의 화합물, 그 염, 에스테르 혹은 아미드를 제조하는 방법.상기식에서 R1은 n이 1에서 7인(CH2)n혹은 a와 b는 각기 0에서 5 이며 a와 b의 합이 5를 넘지 않는 (CH2)aCHCH:CH-(CH2)b이고, R2와 R3는 동일하거나 서로 다른 것으로서 각기 수소, 저급알킬(1에서 4탄소) 또는 질소원자를 지닌 피롤리디노, 피레리디노 혹은 모르폴리노와 같은 헤테로시클릭환(4에서 6환원소), R4A는 수소, 할로겐, 저급알킬(1에서 4탄소원자) 혹은 저급알콕시(1에서 4탄소원자임).
- 청구범위 제1에서 5항중의 어느 하나에 있어서 다음식(Ⅳ)의 화합물 혹은 그 염, 에스테르 혹은 아미드를 제조하는 방법.상기식에서 R1에서 R4는 상기한 대로임.
- 내용 없음
- 청구범위 6항에 있어서 식(Ⅳ)내 R1은 단일 결합 CH=CH혹은 CH2CH2이고 NR2R3는 피롤리디노이고 R4는 메틸 혹은 트리플루오로메틸인 제조방법.
- 청구범위 제1항에서 7항중의 어느 하나에 있어서 CA-CB는 이중결합이고 CH2NR2R2는 함유환에 대하여 트란스인 제조방법.
- 청구범위 제1항에서 5항중의 어느 하나에 있어서 다음식(Ⅴ)의 화합물 혹은 그 염, 에스테르 혹은 아미드를 제조하는 방법.상기식에서 치환기 R1에서 R4는 상술한 대로임.
- 청구범위 9에 있어서 식(Ⅴ)에서 R1은 단일 결합 CH=CH혹은 CH2CH2이고 NR2R3는 디메틸아미노이고 R4는 염소 혹은 브롬인 제조방법.
- 창구범위 1에 있어서 다음에서 선택된 화합물, 그 염, 에스테르 혹은 아미드를 제조하는 방법.(E)-3-(6-(3-피롤리디노-1-(4-톨릴) 프로-1E-에닐(-2-피리딜) 아크릴산.3-(5-(3-피롤리디노-1-(4-톨릴) 프로-1E-에닐)-2-피리딜) 프로피온산.(E)-3-(6-(3-디메틸아미노-1-(4-톨릴) 프로-1E-예염)-2-피리딜) 아크릴산.(E)-3-(5-(3-피롤리디노-1-(4-트리플루오로메틸페닐) 프로-1E-에닐)-2-피리딜) 아크릴산.(E)-3-(6-(3-피롤리디노-1-(4-메톡시페닐) 프로-1E-에닐)-2-피리딜) 아크릴산.(E)-3-(6-(1-페닐-3-피롤리디노프로-1E-에닐)-2-피리딜) 아크릴산.(E)-3-(6-(1-(4-플로로페닐)-3-피롤리디노-1E-에닐)-2-피리딜아크릴산.6-(3-피롤리디오-1-(4-톨릴) 프로-1E-에닐) 피리딘-2-카르복실산.(E)-3-(3-피롤리디노-1-(4-톨릴) 프로-1-에닐) 벤조산.(E)-3-(3-피롤리디노-1-(4-톨릴) 프로-1-에닐) 시남산.(E)-3-((E)-3-피롤리디노-1-(4-메톡시페닐) 프로-1-에닐) 시남산.(E)-3-((E)-3-디메틸아미노-1-(4-톨릴) 프로-1-에닐) 시남산.(E)-3-(3-(3-피롤리디노-1-(4-톨릴) 프로-1-에닐)페닐) 프로피온산.
- 식(Ⅰ)의 화합물과 하나이상의 제약학적으로 알맞는 담체 및 다른 치료적으로 알맞는 성분으로 구성되는 제약학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019870003073A KR870001917B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜화합물의 제조방법 |
| KR1019870003074A KR870001918B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003072A KR870001916B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003071A KR870001915B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003070A KR870001927B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8203261 | 1982-02-04 | ||
| GB8203261 | 1982-02-04 | ||
| GB8229705 | 1982-10-18 | ||
| GB8229705 | 1982-10-18 |
Related Child Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870003073A Division KR870001917B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜화합물의 제조방법 |
| KR1019870003071A Division KR870001915B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003070A Division KR870001927B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003074A Division KR870001918B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003072A Division KR870001916B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840003628A true KR840003628A (ko) | 1984-09-15 |
| KR880001466B1 KR880001466B1 (ko) | 1988-08-11 |
Family
ID=26281898
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830000440A KR880001466B1 (ko) | 1982-02-04 | 1983-02-03 | 피리딜 화합물의 제조방법 |
| KR1019870003072A KR870001916B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003074A KR870001918B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003070A KR870001927B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003071A KR870001915B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003073A KR870001917B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜화합물의 제조방법 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870003072A KR870001916B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003074A KR870001918B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003070A KR870001927B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003071A KR870001915B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜 화합물의 제조방법 |
| KR1019870003073A KR870001917B1 (ko) | 1982-02-04 | 1987-03-30 | 피리딜화합물의 제조방법 |
Country Status (32)
| Country | Link |
|---|---|
| EP (2) | EP0085959B1 (ko) |
| JP (2) | JPS6479153A (ko) |
| KR (6) | KR880001466B1 (ko) |
| AT (2) | ATE64596T1 (ko) |
| AU (1) | AU555083B2 (ko) |
| BG (6) | BG42185A3 (ko) |
| CA (2) | CA1249830A (ko) |
| CS (1) | CS235306B2 (ko) |
| CY (1) | CY1627A (ko) |
| DD (1) | DD209446A5 (ko) |
| DE (2) | DE3379654D1 (ko) |
| DK (1) | DK164662C (ko) |
| ES (6) | ES519491A0 (ko) |
| FI (1) | FI82450C (ko) |
| GB (1) | GB2114565B (ko) |
| GR (1) | GR77407B (ko) |
| HK (1) | HK25892A (ko) |
| HU (1) | HU189223B (ko) |
| IE (1) | IE54600B1 (ko) |
| IL (3) | IL78419A (ko) |
| MC (1) | MC1498A1 (ko) |
| NL (1) | NL930057I2 (ko) |
| NO (2) | NO162556C (ko) |
| NZ (1) | NZ203171A (ko) |
| PH (1) | PH21348A (ko) |
| PL (6) | PL140708B1 (ko) |
| PT (1) | PT76192B (ko) |
| SG (1) | SG106091G (ko) |
| SI (1) | SI8310221A8 (ko) |
| SU (1) | SU1301312A3 (ko) |
| UY (1) | UY23404A1 (ko) |
| YU (1) | YU44821B (ko) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501893A (en) * | 1982-02-04 | 1985-02-26 | Findlay John W A | 3-{6-[3-Pyrrolidino-1-(4-tolyl)prop-1-enyl]-2-pyridyl}acrylic acid and pharmaceutically acceptable salts thereof |
| US4610995A (en) * | 1984-07-27 | 1986-09-09 | Coker Geoffrey G | Certain 1,1-diaryl-propenyl-3-(1-pyrrolidino-2-carboxylic acids, derivatives thereof and their anti-histaminic properties |
| LU86387A1 (fr) * | 1986-04-04 | 1987-12-07 | Oreal | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
| GB8707416D0 (en) * | 1987-03-27 | 1987-04-29 | Wellcome Found | Pharmaceutical formulations |
| DE3711866A1 (de) * | 1987-04-08 | 1988-10-27 | Hoechst Ag | Synthese von peptidamiden mittels festphasenmethode unter verwendung von saeurelabilen ankergruppen |
| GB8914060D0 (en) * | 1989-06-19 | 1989-08-09 | Wellcome Found | Agents for potentiating the effects of antitumour agents and combating multiple drug resistance |
| GB8914040D0 (en) * | 1989-06-19 | 1989-08-09 | Wellcome Found | Agents for potentiating the effects of antitumour agents and combating multiple drug resistance |
| DK0409406T3 (da) * | 1989-06-19 | 1994-02-07 | Wellcome Found | Arylsubstituerede aminderivater, der er anvendelige ved cancerterapi |
| FR2711651B1 (fr) * | 1993-10-28 | 1995-12-22 | Adir | Nouveaux analogues cyclisés de métabolites d'acides gras, leur procédé de préparation et les compositions pharmaceutiques les renfermant. |
| US5420866A (en) * | 1994-03-29 | 1995-05-30 | Scientific-Atlanta, Inc. | Methods for providing conditional access information to decoders in a packet-based multiplexed communications system |
| WO1997006167A1 (en) * | 1995-08-05 | 1997-02-20 | British Biotech Pharmaceuticals Limited | Imidazopyridine derivatives |
| GB9508748D0 (en) * | 1995-04-28 | 1995-06-14 | British Biotech Pharm | Benzimidazole derivatives |
| IT1277597B1 (it) | 1995-09-15 | 1997-11-11 | Smithkline Beecham Spa | Derivati di diarilalchenilammina |
| CN101838235B (zh) * | 2009-06-12 | 2013-08-07 | 重庆华邦制药有限公司 | 3-苯基-3＇-吡啶基丙烯胺类化合物及其合成方法 |
| US20140309244A1 (en) * | 2010-09-23 | 2014-10-16 | Syngenta Participations Ag | Novel microbiocides |
| US20150139896A1 (en) | 2012-04-23 | 2015-05-21 | Saudi Basic Industries Corporation | Solar energy based countinuous process and reactor system for the production of an alkene by dehydrogenation of the corresponding alkane |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567245A (en) * | 1948-05-10 | 1951-09-11 | Schering Corp | Aryl-(2-pyridyl)-amino alkanes and their production |
| DE1227464B (de) * | 1951-09-10 | 1966-10-27 | Wellcome Found | Verfahren zur Herstellung der trans-Form des neuen 1-(4'-Methylphenyl)-1-(2''-pyridyl)-3-pyrrolidinopropens-(1) |
| FR1228802A (fr) * | 1954-05-03 | 1960-09-02 | Farbwerke Hoechst Ag Vomals Me | Procédé de préparation de composés tertio-amino-cétoniques |
| FR2197583B1 (ko) * | 1972-09-07 | 1975-10-17 | Rhone Poulenc Ind |
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1983
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1986
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1987
- 1987-03-30 KR KR1019870003072A patent/KR870001916B1/ko not_active IP Right Cessation
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1988
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1993
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