KR850003534A - N-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법 - Google Patents
N-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법 Download PDFInfo
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- KR850003534A KR850003534A KR1019840007034A KR840007034A KR850003534A KR 850003534 A KR850003534 A KR 850003534A KR 1019840007034 A KR1019840007034 A KR 1019840007034A KR 840007034 A KR840007034 A KR 840007034A KR 850003534 A KR850003534 A KR 850003534A
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- South Korea
- Prior art keywords
- formula
- group
- lower alkyl
- general formula
- compound
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- 125000000623 heterocyclic group Chemical group 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 22
- 239000012442 inert solvent Substances 0.000 claims 15
- -1 2,3-dihydro-2-oxo-1H-benzimidazol-1-yl Chemical group 0.000 claims 9
- 239000003153 chemical reaction reagent Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent 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 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000208202 Linaceae Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 150000000475 acetylene derivatives Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000006477 desulfuration reaction Methods 0.000 claims 1
- 230000023556 desulfurization Effects 0.000 claims 1
- 230000003009 desulfurizing effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 238000001465 metallisation Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229920000642 polymer Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
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- 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
- C07D405/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- 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
- C07D417/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
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Claims (2)
- 다음 일반식(Ⅲ)의 피페리딘을 반응 불활성용매 중에서 다음 일반식(Ⅱ)의 중간체로서 알킬화반응시키거나; 또는 다음 일반식(Ⅳ)의 중간체를 반응불활성용매 중에서 적당한 알킬할라이드, 금속화물 또는 금속염으로 탈황고티화반응시키거나; 또는 다음 일반식(Ⅴ)의 중간체를 적당한 반응불활성용매에서 다음 일반식(Ⅵ)의 피페리딘관 반응시켜 다음 일반식(I-b-1)의 화합물을 제조하거나; 또는 다음 일반식(Ⅶ)의 중간체를 적당한 반응불활성용매 중에서 다음 일반식(Ⅷ)의 피페리딘과 반응시켜 다음 일반식(I-b-2)의 화합물을 제조하거나; 또는 다음 일반식(Ⅸ)의 중간체를 적당한 반응불활성용매 중에서 필요한 경우 화합물(Ⅷ)의 OH기능기를 적당한 아마이 또는 에스테르형성 가능시약과 함께 반응시켜 다음 일반식(I-c)의 화합물을 제조하거나; 또는 다음 일반식(Ⅲ-a)의 피페리딘을 적당한 반응 불활성용매 중에서 다음 일반식(Ⅹ)의 시약과 반응시켜 다음 일반식(I-d)의 화합물을 제조하거나; 또는 다음 일반식(Ⅲ-a)의 중간체를 포름알데히드 또는 이의 중합체 형태 존재하의 적당한 용매중에서 다음 일반식(XI)의 시약과 반응시켜 다음 일반식(I-e)의 화합물을 제조하거나; 또는 다음 일반식(XII)의 중간체를 반응불활성용매 중에서 C=X1발생 시약과 반응시켜 다음 일반식(I-f-1)의 화합물을 제조하거나; 또는 다음 일반식(XIII)의 중간체를 반응불활성 용매중에서 또 필요한 경우에는 적당한 염기존재하에서 고리화반응시켜 다음 일반식(I-f-l-a)의 화합물을 제조하거나; 또는 다음 일반식(XVI)의 중간체를 다음 일반식(XVII)의 산 또는 이의 기능 유도체와 고리화반응시키거나 또는 다음 일반식(XVIII)의 중간체를 적당한 반응불활성용매 중에서 다음 일반식(XIX)의 원자성 아미노산 또는 티오산과 반응시켜 다음 일반식(I-f-2)의 화합물을 제조하거나; 또는 다음 일반식(XVI)중간체를 적당한 용매중에서 다음 일반식(XX)의 아세틸렌 유도체와 반응시켜 다음 일반식(I-f-3)의 화합물을 제조하거나; 또는 다음 일반식(XXI)의 시약을 적당한 반응불활성용매중에서 다음 일반식(XXII)의 중간체와 반응시켜 다음 일반식(I-f-4)의 화합물을 제조하거나; 또는 다음 일반식(XXIII)의 시약을 적당한 반응불활성용매 중에서 다음 일반식(XXIV)의 중간체와 고리화반응시켜 다음 일반식(I-f-5)의 화합물을 제조하거나; 또는 다음 일반식(XXV)의 시약을 적당한 반응불활성용매 중에서 CS2로서 고리화반응시켜 다음 일반식(I-f-6)의 화학물을 제조하거나; 또는 다음 일반식(XXVI)의 시약을 적당한 반응불활성용매 중에서 다음 일반식(XXVII)의 중간체와 반응시켜 다음 일반식(I-f-7)의 화합물을 제조하거나 ; 또는 다음 일반식(XXVIII)의 중간체를 반용불활성용매 중에서 적당한 알킬할라이드, 금속산화물 또는 금속염으로 탈황고리화반응시켜 다음 일반식(I-f-8)의 화합물을 제조하거나; 또는 다음 일반식(XXIX)의 중간체를 반응불활성용매 중에서발생시약과 반응시켜 다음 일반식(I-f-9)의 화합물을 제조하거나; 또는 다음 일반식(XXX)의 중간체를 적당한 용매중에서 착화합 금속수소화물로서 환원시켜 다음 일반식(I-g)의 화합물을 제조함을 특징으로 하여 다음 일반식(Ⅰ)의 N-(비사이클 헤테로사이클릴)-4-피페리딘아민, 이의 약제학적으로 허용되는 산부가염 및 입체화학적 이성체를 제조하는 방법.Het-CsH2s-Y-Alk'-C(O)-D (XXX)Het-CsH2s-Y-Alk'-CH2-D (I-g)상기에서, A1=A2-A3=A4는 다음 일반식(a)(b)(c)(d) 또는 (e)를 갖는 2가의 레디칼로서 이들 레디칼중의 1개 또는 2개 수소원자가 할로, 저급알킬, 저급알킬옥시, 트리플루오로메틸 또는 하이드록시로서 상호독립해서 치환될수 있으며; R는 수소 및 저급 알킬로 구성되는 군에서 선정한 것이고; R1은 수소, 알킬, 사이클로알틸, Ar1과 1개 또는 2개의 Ar1기로 치환된 저급 알킬로 구성되는 군에서 선정한 것이며; R2는 수소, 저급알킬, 사이클로알킬,(저급알킬(저급알킬)-CO-, 및 저급알킬-O-(CO)- 및 Ar2-저급알킬로 구성되는 군에서 선정한 것이고; L은 다음 일반식(f)(g) 및 (h)의 레디칼로 구성된 군에서 선정한 것으로, 이때 n은 0 또는 1 또는 2의 정수이고, S는 0 또는 1내지 6포함 정수이며, Alk는 저급알칸디일이고, Y는 O,S,NR3또는 직접 결합손이며, X는 O,S,CH-NO2또는 NR4이고, Z는 O,S,NR5또는 직접결합손이고, 또 Het는 1개 이상의 질소원자를 갖는 임의 치환된 5원 또는 6원 헤테로사이클 고리로서, 임의 치환된 5원 또는 6원 고리와 융합될 수 있으나, Het가 CsH2s와 탄소상에서 결합되는 경우에는, 이 5원- 또는 6원- 고리는 임의 치환된 벤젠고리와는 헥융합하지 않으며; L이 일반식(f) 또는 Y가 직접 결합손이 아닌 일반식(g) 또는 Z가 직접결합손이 아닌 일반식(h)중 1개의 레디칼인 경우, 이 레디칼중의 Het는 CsH2s와 질소상에서 결합되며, 또 S가 0이 아니고: A1=A2-A3=A4가 일반식(a) 또는 (b)의 레디칼이고, L이 S가 0이고 또 Y가 직접결합손인 일반식(g)의 레디칼인 경우, Het는 2,3-디하이드로-2-옥소-1H-벤즈이미다졸-1-일 또는 2,3-디하이드로-3-옥소-벤즈옥사진-4-일기가 아니라는 조건을 만족하며; 전술한 R3가 수소,저급알킬, (Ar2)저급알킬, 2-저급알킬옥시-1,2-디옥소에틸 또는 일반식 -C(=X)-R6의 기로서 R6는 수소 , 저급알킬,Ar2,Ar2-저급알킬, 저급알킬옥시, Ar2-저급알킬옥시, 모노-또는 디(저급알킬)아미노, Ar2-아미노, Ar2-저급알킬아미노 또는 Ar2-저급알킬(저급알킬)아미노이고; 전술한 R4는 수소, 저급알킬, 시아노, 니트로, Ars-설포닐, 저급알킬설포닐, 저급알킬카르보닐 또는 Ar2-카르보닐이며; 또 전술한 R5는 수소 또는 저급알킬이고; 또 Ar1은 할로, 하이드록시, 니트로, 시아노, 트리플루오로메틸, 저급알킬, 저급알킬옥시, 저급알킬티오, 메트캅토, 아미노, 모노- 및 디(저급알킬)아미노, 카르복실, 저급알킬옥시카르보닐과 저급알길-CO-로 구성되는 군으로부터 각각 독립해서 선정한 3개까지의 치환체로 임의 치환한 페닐; 티에닐; 할로티에닐; 푸라닐; 저급알킬 치환 푸라닐; 피리디닐; 피라지닐; 저급알킬로 임의 치환된 티아졸릴 및 이미다졸릴로 구성되는 군에서 선정한 것이며; 또 Ar2는 할로, 하이드록시, 니트로, 시아노, 트리플루오로메틸, 저급알킬, 저급알킬옥시, 저급알킬티오, 메르캅토, 아미노, 모노- 및 디(저급알킬)아미노, 카르복실, 저급알킬옥시카르보닐 및(저급알킬)-CO-로 구성되는 군으로부터 각각 독립해서 선정한 3개 까지의 치환체로 임의 치환한 페닐로 구성되는 군에서 선정한 것이며, Q2가 수소, Q1이 Het와 결합해서 W가 클로로, 브로모 또는 요드 등의 할로 또는 메틸설포닐옥시 또는 4-메틸페닐설포닐옥시 등의 설포닐옥시기와 같은 적합한 반응이탈기인 일반식 L-W의 기를 형성하고; Q1이 W1가 전술한 W의 정의 이욍 S가 0일 때 W1가 또한 저급알킬옥시 또는 저급알킬티오기라는 조건하에 일반식 -CsH2s-W1의 기이고 또 Q2는 일반식기인 경우 다음 일반식(I-a-1)의 화합물을 제조하고; Q1이 전술한 조건이 -CsH2s-W1의 기이고, 또 Q2가 Y1가 직접결합손을 제외하고는 앞의 Y의 정의와 동일한 일반식 HY1-Alk-의 기인 경우, 다음 일반식(I-a-2)의 화합물을 제조하며; Q1이 전술한 조건의 -CsH2s-W1의 기이고 또 Q2가 Z1가 직접 결합손을 제외하고는 앞의 Z의 정의와 동인한 일반식 HZ1-C(X)-Y-Alk-의 기인 경우, 다음 일반식(I-a-3)의 화합물을 제조하고; Q1이 일반식 -CsH2s-Y1H의 기이고 또 Q2가 일반식 W-Alk-의 기인 경우 다음 일반식(I-a-2)의 화합물을 제조하며 또 Q1이 일반식 -CsH2s-Z-C(X)-Y1H의 기이고 또 Q2가 일반식 W-Alk-의 기인 경우 다음 일반식(I-a-4)의 화합물을 제조하고; 또 X1은 O 또는 S 이며, B3는 -CH=CH-CH=CH-,-S-CH=CH- 또는 -N=CH-NH-이고; R7, R10, R17, R19는 수소, 저급알킬, Ar2-저급알킬, 하이드록시저급알킬 또는 저급알킬옥시카르보닐로 구성되는 군으로부터 선정된 것이며; W2는 적당한 반응이탈기이고; R11-a는 (C1-5)알킬 또는 (저급알킬옥시카르보닐)(C1-5)알킬이며; B4는 -CH2-NH-(CH2)2-, -N=CH-CH=CH- 또는 -N=CH-N=CH-이고; B5는 -N=CH-CH=CH-, -CH=CH-N=CH- 또는 -CH=N-CH=N-이며; B6는 -CH-CH=CH- 또는 -CH=N-CH=N- 이고; Alk'는 1개의 메틸렌기가 부족하다는 조건하에서 앞의 Alk정의와 동일하며, 또 D는 일반식의 기이고, 또 K는 다음 일반식(j-1)(j-2) 또는 (j-3)의 2가 기이다.-CH=CH-CH=CH- (a) -N=CH-CH=CH- (b)-CH=N-CH=CH- (c) -CH=CH-N=CH- (d)
- 제1항에 있어서, 화합물을 3-[2-[4-[[3-(2-푸라닐메틸)-3H-이미다조[4,5-b]피리딘-2-일]아미노-1-피페리디닐]에틸]-2-메틸-4H-피리도[1,2-a]피리미딘-4-온으로 구성되는 군으로부터 선정한 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US5258380A (en) * | 1985-06-24 | 1993-11-02 | Janssen Pharmaceutica N.V. | (4-piperidinylmethyl and -hetero)purines |
US4943580A (en) * | 1987-03-09 | 1990-07-24 | Janssen Pharmaceutica N.V. | Anti-histaminic benzimidazole, imidazopyridine and purine derivatives |
US4897401A (en) * | 1987-06-19 | 1990-01-30 | Janssen Pharmaceutical N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases |
US5151424A (en) * | 1987-07-01 | 1992-09-29 | Janssen Pharmaceutica N.V. | Pharmacologically active (Bicyclic heterocyclyl)methyl and -hetero) substituted hexahydro-1H-azepines and pyrrolidines |
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US5272150A (en) * | 1989-04-07 | 1993-12-21 | Janssen Pharmaceutica N.V. | Hydroxyalkylfuranyl derivatives |
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US5217980A (en) * | 1990-07-19 | 1993-06-08 | Janssen Pharmaceutica N.V. | Oxazolyl and piperidinyl substituted benimidazolyl compounds |
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US5739330A (en) * | 1996-02-05 | 1998-04-14 | Hoechst Celanese Corporation | Process for preparing quinazolones |
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---|---|---|---|---|
US3960863A (en) * | 1974-06-25 | 1976-06-01 | Sankyo Company Limited | Pyrido[1,2-a]pyrimidinone derivatives |
JPS525797A (en) * | 1975-06-28 | 1977-01-17 | Sankyo Co Ltd | Preparation of tetrahydropyrido pyrimidinone derivatives |
JPS525796A (en) * | 1975-06-28 | 1977-01-17 | Sankyo Co Ltd | Preparation of tetrahydropyrido pyrimidinone derivatives |
US4219559A (en) * | 1979-01-10 | 1980-08-26 | Janssen Pharmaceutica N.V. | N-Heterocyclyl-4-piperidinamines |
US4342870A (en) * | 1980-03-28 | 1982-08-03 | Janssen Pharmaceutica N.V. | Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives |
US4485107A (en) * | 1982-11-01 | 1984-11-27 | Janssen Pharmaceutica N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones |
-
1984
- 1984-10-12 US US06/660,608 patent/US4695569A/en not_active Expired - Fee Related
- 1984-11-09 KR KR1019840007034A patent/KR880000044B1/ko not_active IP Right Cessation
- 1984-11-23 SU SU843814401A patent/SU1500162A3/ru active
- 1984-11-29 ZA ZA849331A patent/ZA849331B/xx unknown
- 1984-11-29 PL PL1984250633A patent/PL146377B1/pl unknown
-
1987
- 1987-09-17 SU SU874203318A patent/SU1694064A3/ru active
Also Published As
Publication number | Publication date |
---|---|
SU1500162A3 (ru) | 1989-08-07 |
KR880000044B1 (ko) | 1988-02-20 |
SU1694064A3 (ru) | 1991-11-23 |
US4695569A (en) | 1987-09-22 |
PL250633A2 (en) | 1985-12-17 |
ZA849331B (en) | 1986-07-30 |
PL146377B1 (en) | 1989-01-31 |
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