KR850004478A - 퀴놀온의 제조방법 - Google Patents
퀴놀온의 제조방법 Download PDFInfo
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- KR850004478A KR850004478A KR1019840008229A KR840008229A KR850004478A KR 850004478 A KR850004478 A KR 850004478A KR 1019840008229 A KR1019840008229 A KR 1019840008229A KR 840008229 A KR840008229 A KR 840008229A KR 850004478 A KR850004478 A KR 850004478A
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- KR
- South Korea
- Prior art keywords
- alkyl
- formula
- compound
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- het
- Prior art date
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- 238000000034 method Methods 0.000 title claims 12
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims 2
- -1 C 4 alkyl halides Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 231100000331 toxic Toxicity 0.000 claims 6
- 230000002588 toxic effect Effects 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000010520 demethylation reaction Methods 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000007324 demetalation reaction Methods 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000011535 reaction buffer Substances 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl 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
- C07D213/24—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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D215/18—Halogen atoms or nitro 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
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
-
- 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
- C07D215/48—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
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D417/02—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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
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Claims (15)
- 일반식(Ⅱ)의 화합물을 탈메틸화시켜 R2가 H인 일반식(Ⅰ)의 화합물을 생성시킨 후(a) 에스테르화 반응에 의해서 3위치의 -COOH기를 -COO (C1내지 C4알킬)기로 전환; (b) 환원 반응에 의해서 니트로기인 R1을 아미노기로 전환; (C) 할로겐화 반응에 의해서 수소 원자인 R1을 C1,Br 또는 I로 전환; (d) 과산 산화제를 사용하여 질소함유헤테로사이클인 "Het"를 N-옥사이드로 산화; (e) 강염기와 반응시킨후 각각 C1내지 C4알킬 할라이드 또는 디(C1내지 C4알킬) 술페이트, 또는 2-히드록시에틸 할라이드와 반응시켜 수소원자 인 R2를 C1내지 C4알킬 또는 2-히드록시 에틸기로 전환; (f) 촉매적 수소화 반응에 의해서 3-및 4-위치사이에 이중결합을 갖는 일반식(Ⅰ)의 생성물을 3,4-디히드로유도체로 전환; (g) 황산은 및 진한 황산의 존재하에 염소, 브롬 또는 요오드와 반응시켜 일반식(Ⅰ) 3,4-디히드로퀴놀온의 8-위치의 R인 수소원자를 각각 Cl, Br, I로 전환; (h) 아세트산중의 브롬 및 나트륨 아세테이트와 반응시켜 일반식(Ⅰ)의 3,4-디히드로 생성물을 3,4-디히드로 생성물을 3-및 4-위치사이에 이중 결합을 갖는 일반식(Ⅰ)의 화합물로 전환; (i) 구리 (I)촉매의 존재하에 C1내지 C4알킬 티올의 염과 반응시켜 8-위치의 할로겐원자를 C1내지 C4알킬티오기로 전환; (j) 적량의 유기과산 또는 나트륨 메타퍼요오데이트와 반응시켜 C1내지 C4알킬티오기인 R을 C1내지 C4알콕시기인 R을 히드록시기로 전환; (l) C1내지 C4알킬리 및 포름알데히드와 차례로 반응시켜 8-위치의 R이 Cl, Br 또는 I인 일반식(Ⅰ)의 생성물을 약제학적으로 무독한 그의 산부가염으로 전환; 및 (m) 적절한 산과 방응시켜 일반식(Ⅰ)의 생성물을 약제학적으로 무독한 그의 산부가염으로 전환; 및 (n) 적절한 염기와 반응시켜 일반식(Ⅰ)의 생성물을 금속염으로 전환시키는 공정중 임의로 하나 또는 그 이상을 수행함을 특징으로하여, 다음 일반식(I)의 화합물 또는 약제학적으로 무독한 그의염을 제조하는 방법.상기식에서, "Het"는 퀴놀은 환의 5-, 6-, 또는 8-위치에 탄소에 의해 결합된 임의로 치환된 5-또는 6월 모노시클릭 방향족 헤테로시클릭기이며; R은 5-, 6-, 7- 또는 8-위치에 결합되며, 수소, C1내지 C4알킬, C1내지 C4알콕시, C1내지 C4알킬티오, C1내지 C4알킬술피닐, C1내지 C4알킬술포닐, 할로, CF3, 히드록시, 히드록시메틸 또는 시아노이며; R1은 수소, 시아노, (C1내지 C4알콕시)카보닐, C1내지 C4알킬, 니트로, 할로, -NR3R4또는 -CONR3R4이며, 이때 R3및 R4는 각각 독립적으로 H 또는 C1내지 C4알킬이거나, 이들이 결합된 질소원자와 함께 O, S 및 N-R5(여기서, R5는 수소 또는 C1내지 C4알킬이다)로부터 선정된 이종원자 또는 기를 임의로 하나더 함유하는 포화된 5- 또는 6-원 헤테로 시클릭기를 형성하며; R2는 H, C1내지 C4알킬 또는 2-히드록시에틸이며; Y는 H 또는 C1내지 C4알킬이고; 3-4-위치사이의 점선을 임의의 결합을 나타낸다.
- 제1항에 있어서, 탈메탈화 반응이 무기산을 사용하여 수행되는 방법.
- 제2항에 있어서, 탈메틸화반응이 수성 HBr, 수성 HCI 또는 5내지 15용적%의 수성 HBr을 함유하는 에탄올을 사용하여 수행되는 방법.
- 제1내지 3항중 어느한 항에 있어서, 반응을 실온내지 용액의 환류온도까지의 온도에서 수행하는 방법.
- 일반식(Ⅲ)의 화합물과 일반식 Het-zn-CI의 화합물("Het"는 제1항에서의 정의와 같다)을 구조식pd(ppha3)4촉매의 존재하에 반응시키고, 제1항에서 정의된 (a)내지 (n)공정중 하나 또는 그 이상을 임의로 수행함을 특징으로 하여 제1항에서 정의된 일반식(Ⅰ)의 화합물 또는 약제학적으로 무독한 그의 염을 제조하는 방법.상기식에서, R,R1,R2,Y 및 점선은 제1항에서의 정의와 같고, θ는 이탈기이다.
- 제5항에 있어서, 반응이 실온 내지 혼합물의 환류온도까지의 온도에서 유기용매중에서 수행되며, Q가 C1,Br 또는I인 방법.
- 일반식(Ⅳ)의 화합물을 폐환시켜 R1, R2및 T가 H인 일반식(Ⅰ)의 화합물을 생성시킨 후, 제1항에서 정의된 (a) 및 (c)내지 (n)의 공정중 하나 또는 그 이상을 임의로 수행함을 특징으로하여 제1항에서 정의된 일반식(Ⅰ)의 화합물 또는 약제학적으로 무독한 그의 염을 제조하는 방법.상기식에서, "Het" 및 R은 제1항의 정의와 같고, θ는 이탈기이다.
- 제7항에 있어서, θ가 메톡시 또는 에톡시이며, 폐환반응이 진한황산중에서 수행됨이 특징인 방법.
- 제1항 내지 6항중 어느한 항에 있어서, R이 수소, C1내지 C4알킬, C1내지 C4알콕시, C1내지 C4알킬디오, C1내지 C4알킬 슬피닐, C1내지 C4알킬술포닐, 할로, CF3, 히드록시 또는 히드록시메틸인 방법.
- 제9항에 있어서, R이 7-또는 8-위치에 결합되는 H,C1내지 C4알킬, 메톡시, 메틸티오, 메틸술피닐, 메틸술포닐, 브로모, 히드록시 또는 히드록시메틸이고; R1이 H, 시아노, 메톡시, 카보닐, 니트로, 브로모 또는 아미노이고; R2가 H 또는 CH3이고; 5-, 6-또는 7-위치에 결합된 "Het"가 피리딜, 그의 N-옥사이드, 피리미딘일 피리다진일, 피라진일, 이미다졸릴, 트리아졸릴, 레트라졸릴, 티아졸릴, 옥사디아졸릴, 티에닐 또는 무틸로서, 모두가 C1내지 C4알킬, C1내지 C4알콕시, 시아노, 아미노 및 카바모일에서 각각 선정된 1 또는 2치환체에 의해서 임의로 치환되었으며; 3-및 4-위치사이에 이중 결합이 있고; Y가 H 또는 CH3인 방법.
- 제10항에 있어서, "Het"가 (a) 1 또는 2개의 메틸기 또는 단일 메톡시, 시아노, 아미노 또는 카바모일기에 의해 임의로 치환된 피리딜 (b) 피리딜-N-옥사이드 (c) 피리미딘일 (d) 피리다진일 (e) 피라진일 (f) 트리아졸일 또는 N-메틸트리아졸일 (g) 테트라졸릴 또는 N-(n-부틸)-테트라졸일 (h) N-메틸이미다졸 (i) 릴옥사디아졸 (j) 릴티아졸일 (k) 티에닐 및 (l) 푸릴로부터 선정되는 방법.
- 제11항에 있어서, 일반식(IA)의 화합물을 제조하는 방법.상기식에서, "Het"은 제11항의 정의와 같으며, R은 제10항의 정의와 같다.
- 제1내지 6항중 어느한 항에 있어서, "Het"가 퀴놀몬의 5-, 6-, 7-또는 8-위치에 탄소에 의해 결합된 임의로 치환된 5- 또는 6-원 모노시클릭 방향족 질소함유 헤테로 시클릭기이며; R이 5-, 6-, 7-또는 8-위치에 결합되며, 수소, C1내지 C4알킬 또는 C1내지 C4알콕시이며; R1이 수소, 시아노,(C1내지 C4알콕시)카보닐;C1내지 C4알킬, CONR3R4또는 -NR3R4이며, 이때 R3및 R4는 각각 독립적으로 H 또는 C1내지 C4알킬이거나 이들이 결합된 질소 원자와 함께 O, S 및 N-R5(여기서 R5는 H 또는 C1내지 C4알킬이다)로부터 선정된 이종원자 또는 기를 임의로 하나 더 함유하는 포화된 5-또는 6-원 헤테로시클릭기를 형성하며; R2가 H,C1내지 C4알킬 또는 2-히드록시에틸이고; Y가 H 또는 CH3이며;3- 및 4-위치사이의 점선이 임의 결합인 일반식(Ⅰ)의 화합물 또는 약제학적으로 무독한 그의 염의 제조방법.
- 제1내지 6항중 어느한 항에 있어서, R1,R2및 Y가 모두 H이며, R이 CH3로서 3-위치에 결합되며, 3-및 4-위치사이에 이중결합이 있으며, "Het"가 6-위치에 결합된 2,6-디메틸피리드-3-일 또는 1-메틸-(1H)-1,2,4-트리아졸-5-일인 일반식(Ⅰ)의 화합물의 제조방법.
- 제14항에 있어서, "Het"가 2,6-디메틸피리드-3-일이고, 생성물을 수산화나트륨과 반응시켜 나트륨염으로 전환시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838334282A GB8334282D0 (en) | 1983-12-22 | 1983-12-22 | Quinolone inotropic agents |
| GB8334282 | 1983-12-22 | ||
| GB8417340 | 1984-07-06 | ||
| GB848417340A GB8417340D0 (en) | 1984-07-06 | 1984-07-06 | Quinoline inotropic agents |
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| Publication Number | Publication Date |
|---|---|
| KR850004478A true KR850004478A (ko) | 1985-07-15 |
| KR870000911B1 KR870000911B1 (ko) | 1987-05-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840008229A KR870000911B1 (ko) | 1983-12-22 | 1984-12-21 | 퀴놀온의 제조방법 |
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| Country | Link |
|---|---|
| US (1) | US4710507A (ko) |
| EP (1) | EP0148623A3 (ko) |
| KR (1) | KR870000911B1 (ko) |
| AU (1) | AU556494B2 (ko) |
| CA (1) | CA1253497A (ko) |
| CS (1) | CS249533B2 (ko) |
| DK (1) | DK619584A (ko) |
| ES (1) | ES8603863A1 (ko) |
| FI (1) | FI845036L (ko) |
| GR (1) | GR82511B (ko) |
| HU (1) | HUT36472A (ko) |
| IL (1) | IL73877A (ko) |
| NO (1) | NO845228L (ko) |
| NZ (1) | NZ210670A (ko) |
| PL (1) | PL144816B1 (ko) |
| PT (1) | PT79699B (ko) |
| SU (1) | SU1407397A3 (ko) |
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| BR112014006283B1 (pt) * | 2011-09-15 | 2021-11-03 | F. Hoffmann-La Roche Ag | Novos derivados de dihidroquinolina-2-ona |
| PT2785695T (pt) | 2011-11-30 | 2020-08-20 | Hoffmann La Roche | Novos derivados bicíclicos de dihidroisoquinolina-1-ona |
| KR20150070348A (ko) | 2012-10-16 | 2015-06-24 | 얀센 파마슈티카 엔.브이. | RoRγt의 헤테로아릴 결합 퀴놀리닐 조절제 |
| CN105073729A (zh) | 2012-10-16 | 2015-11-18 | 詹森药业有限公司 | RORγt的苯基连接的喹啉基调节剂 |
| PL2909192T3 (pl) | 2012-10-16 | 2017-09-29 | Janssen Pharmaceutica Nv | Połączone metylenem modulatory chinolinylowe ROR-GAMMA-T |
| EP2964628B1 (en) | 2013-03-08 | 2019-09-11 | F.Hoffmann-La Roche Ag | New dihydroquinoline-2-one derivatives as aldosterone synthase (cyp11b2 or cyp11b1) inhibitors |
| SI3004077T1 (sl) * | 2013-05-27 | 2020-01-31 | F. Hoffmann-La Roche Ag | Novi spojini 3,4-dihidro-2H-izokinolin-1-on in 2,3-dihidro-izoindol-1-on |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| WO2015057629A1 (en) | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | ALKYL LINKED QUINOLINYL MODULATORS OF RORyt |
| WO2015057626A1 (en) | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | QUINOLINYL MODULATORS OF RORyT |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| CN115504933A (zh) * | 2022-10-13 | 2022-12-23 | 广东工业大学 | 一种多取代喹啉酮化合物的制备方法及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907808A (en) * | 1971-05-17 | 1975-09-23 | Sterling Drug Inc | 1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives |
| US3962445A (en) * | 1973-05-19 | 1976-06-08 | Beecham Group Limited | Anti-allergenic carbostyril derivatives |
| US3993656A (en) * | 1974-11-19 | 1976-11-23 | Merck & Co., Inc. | 1,8-Naphthyridine compounds |
| JPS5473783A (en) * | 1977-11-15 | 1979-06-13 | Otsuka Pharmaceut Co Ltd | Pyridine derivative |
| FR2439196A1 (fr) * | 1978-10-17 | 1980-05-16 | Yoshitomi Pharmaceutical | Nouveaux derives de la pyridazinone utilisables en therapeutique comme agents anti-thrombotiques et anti-hypertenseurs |
| US4258185A (en) * | 1978-10-17 | 1981-03-24 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridazinone compounds |
| JPS5777676A (en) * | 1980-10-31 | 1982-05-15 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| EP0102046A1 (en) * | 1982-08-26 | 1984-03-07 | Schering Corporation | Tricyclic lactams, method for making them, pharmaceutical compositions containing them |
-
1984
- 1984-12-18 PT PT79699A patent/PT79699B/pt unknown
- 1984-12-18 US US06/683,440 patent/US4710507A/en not_active Expired - Lifetime
- 1984-12-19 GR GR82511A patent/GR82511B/el unknown
- 1984-12-19 CS CS8410000A patent/CS249533B2/cs unknown
- 1984-12-19 ES ES538805A patent/ES8603863A1/es not_active Expired
- 1984-12-19 FI FI845036A patent/FI845036L/fi not_active Application Discontinuation
- 1984-12-19 EP EP84308925A patent/EP0148623A3/en not_active Withdrawn
- 1984-12-20 IL IL73877A patent/IL73877A/xx unknown
- 1984-12-20 CA CA000470605A patent/CA1253497A/en not_active Expired
- 1984-12-20 NZ NZ210670A patent/NZ210670A/en unknown
- 1984-12-20 PL PL1984251092A patent/PL144816B1/pl unknown
- 1984-12-21 AU AU37017/84A patent/AU556494B2/en not_active Ceased
- 1984-12-21 DK DK619584A patent/DK619584A/da not_active Application Discontinuation
- 1984-12-21 HU HU844800A patent/HUT36472A/hu unknown
- 1984-12-21 KR KR1019840008229A patent/KR870000911B1/ko not_active IP Right Cessation
- 1984-12-21 SU SU843826174A patent/SU1407397A3/ru active
- 1984-12-21 NO NO845228A patent/NO845228L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ210670A (en) | 1987-03-31 |
| IL73877A (en) | 1988-10-31 |
| PT79699B (en) | 1986-12-10 |
| ES538805A0 (es) | 1986-01-01 |
| NO845228L (no) | 1985-06-24 |
| DK619584A (da) | 1985-06-23 |
| SU1407397A3 (ru) | 1988-06-30 |
| GR82511B (en) | 1985-04-22 |
| CS249533B2 (en) | 1987-03-12 |
| PL144816B1 (en) | 1988-07-30 |
| FI845036A0 (fi) | 1984-12-19 |
| EP0148623A2 (en) | 1985-07-17 |
| DK619584D0 (da) | 1984-12-21 |
| EP0148623A3 (en) | 1986-06-04 |
| PT79699A (en) | 1985-01-01 |
| AU556494B2 (en) | 1986-11-06 |
| AU3701784A (en) | 1985-07-04 |
| PL251092A1 (en) | 1985-12-17 |
| HUT36472A (en) | 1985-09-30 |
| IL73877A0 (en) | 1985-03-31 |
| FI845036L (fi) | 1985-06-23 |
| CA1253497A (en) | 1989-05-02 |
| KR870000911B1 (ko) | 1987-05-06 |
| US4710507A (en) | 1987-12-01 |
| ES8603863A1 (es) | 1986-01-01 |
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