KR850002259A - 히스타민 h₂- 섭수체 길항 작용을 가진 2,5-디치환-4(3h)- 피리미돈튜의 제조방법 - Google Patents
히스타민 h₂- 섭수체 길항 작용을 가진 2,5-디치환-4(3h)- 피리미돈튜의 제조방법 Download PDFInfo
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- KR850002259A KR850002259A KR1019840005791A KR840005791A KR850002259A KR 850002259 A KR850002259 A KR 850002259A KR 1019840005791 A KR1019840005791 A KR 1019840005791A KR 840005791 A KR840005791 A KR 840005791A KR 850002259 A KR850002259 A KR 850002259A
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- -1 2,5-disubstituted-4 (3H) -pyrimidone Chemical class 0.000 title claims 13
- 238000000034 method Methods 0.000 title claims 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title 2
- 230000008485 antagonism Effects 0.000 title 1
- 229960001340 histamine Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 239000007810 chemical reaction solvent Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000010992 reflux Methods 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 231100000252 nontoxic Toxicity 0.000 claims 4
- 230000003000 nontoxic effect Effects 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 125000005495 pyridazyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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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
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- A—HUMAN NECESSITIES
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/096—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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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- 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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- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 메탄올 또는 에탄올 등의 불활성 반응 용매의 존재하에 바람직하게는 환류 온도에서 다음 구조식의 화합물, A－(CH2)mZ(CH2)nNH2[여기서, A는 페닐, 푸릴, 티에닐, 피리딜, 티아졸릴, 이미다졸릴, 옥사졸릴, 옥사디아졸릴, 티아디아졸릴, 트리아졸릴, 이속사졸릴, 이소티아졸릴, 피리미디닐, 피라졸릴, 피리다지릴 또는 피라졸릴이 될 수 있는데, 단 A에는 한개 또는 두개의 치환체가 포함될 수 있는데, 그 하나의 치환체는및 －(CH2)qNR6R7(여기서, q는 0 내지 6의 정수이고, R4는 수소원자, 한개 이상의 수소 원자로 임의 치환된 (저급)알킬기(단, 질소 원자에 결합된 탄소 원자에는 할로겐 원자가 없다), 시클로 (저급)알킬, 시클로(저급)알킬(저급)알킬, (저급)알카노일 또는 벤조일기이며, R6및 R7은 각각 수소, (저급)알킬, (저급)알케닐, (저급)알키닐, 페닐(저급)알킬 또는 (저급)알콕시 (저급)알킬이거나(이때, (저급)알콕시 모핵은 질소 원자로부터 제거된 두 개 이상의 탄소 원자이다), 또는 R6및 R7은 질소 원자와 결합하여 피롤리디노, 메틸피롤리디노, 디메틸피롤리디노, 모르폴리노, 티오모르폴리노,ㅡ 피페리디노, 메틸피페리디노, 디메틸피페리디노, 히드록시피페리디노, N－메틸피페라지노, 호모피페리디노, 헵타메틸렌이미노, 옥타메틸렌이미노 또는 3－아자비시클로[3.2.2]논－3－일로 될 수 있다) 중에서 선택되고, 다른 하나의 치환체는 (저급)알킬, 히드록시, 트리플루오르메틸, 하로겐, 아미노, 히드록시메틸 및 (저급)알킬 중에서 선택되며, m은 0 내지 2의 정수이고, z는 황, 산소 또는 메틸렌이며, n은 2 내지 5의 정수이다]를 다음 구조식의 화합물,[여기서, R1은 NO2또는 NR2R3(이때, R2및 R3은 각각 수소 또는 (저급)알킬이거나, 또는 R2가 수소일 때 R3역시 포르밀, 카르브알콕시, 알카노일 또는 벤조일이 될 수 있고, R8은 플루오르, 클로로, 브로모, 요오드, 알킬티오, 니트로아미노, 펜옥시, 치환 펜옥시와 같은 이탈기이다]과 반응시켜서 R1이 NO2인 아래 구조식(Ⅰ)의 화합물을 얻고, R1이 NR2R3일 때 이 R2및 R3가 각각 수소인 화합물을 얻고자 하는 경우에는 R1이 NO2인 화합물을 라니 니켈 존재하에 수소 가스로 환원시키고, R1이 NR2R3일 때 R2가 수소, R3이 포르밀인 화합물을 얻고자 하는 경우에는 R1이 NR2R3이고, 이 R2및 R3이 각각 수소인 화합물을 포름산페닐과 반응시키고, 제약상 허용되는 비독성 산부가염을 얻고자 할 때에는 구조식(Ⅰ)의 화합물로 부터 공지의 방법으로 그 산부가염을 얻는 것이 특징인 다음 구조식(Ⅰ)의 2,5－디치환－4(3H)－피리미돈류,[여기서, A,m,Z,n 및 R1은 앞에서 정의한 바와 같다] 및 그의 제약상 허용되는 비독성 산부가염의 제조 방법.
- 메탄올 또는 에탄올 등의 불활성 반응 용매의 존재하에 바람직하게는 환류 온도에서 다음 구조식의 화합물,A－(CH2)mZ(CH2)nNH2[여기서, A,m,Z 및 n은 제1항에서 정의한 바와 같다]를 다음 구조식의 화합물,[여기서, R9는 티오알킬 또는 구조식,로 나타내는 기이다]과 반응시켜서 다음 구조식(Ⅱ)의 화합물,(Ⅱ)[여기서, A,m,Z 및 n은 앞에서 정의한 바와 같다]를 얻고, 이 화합물을 다음 구조식의 화합물,[여기서, R10은 수소 또는 저급 알킬이고, R11은 저급알킬, 아릴, 알콕시 또는 아릴옥시인데, R10이 수소이고 R11은 에톡시인 것이 바람직하다]와 반응시켜서 다음 구조식(Ⅲ)의 화합물,[여기서, A,m,Z,n,R10및 R11은 앞에서 정의한 바와 같다]를 얻은 다음, 이 화합물을 가수분해하여 아래 구조식(Ⅰ)에서 R1이 NR2R3이고 이때 R2및 R3이 각각 수소인 화합물을 얻고, 이들의 제약상 허용되는 비독성 산부가염을 얻고자 할 때에는 구조식(Ⅰ)의 화합물로 부터 공지의 방법으로 그 산부가염을 얻는 것이 특징인 다음 구조식(Ⅰ)의 2,5－디치환－4(3H)－피리미돈류,[여기서, A,m,Z,n 및 R1은 앞에서 정의한 바와 같다] 및 그의 제약상 허용되는 비독성 산부가염의 제조 방법.
- 불활성 반응 용애 존재하에 실온 내지 용매의 환류 온도에서 다음 구조식의 화합물,[여기서, R8은 제1항에서 정의한 바와 같다]을 다음 구조식의 화합물,HSCH2CH2NH2와 반응시켜서 다음 구조식(Ⅳ)의 화합물,를 얻고, 이 화합물을 다음 구조식의 화합물,A－(CH2)mX[여기서, A 및 m은 제1항에서 정의한 바와 같고, X는 플루오로, 클로로, 브로모, 요오도, －O2SR12(여기서, R12는 메탄술포네이트와 같은 저급 알킬릴이다), －O2SR13(여기서, R13은 아릴이거나, 또는 벤젠술포네이트, P－브로모 벤젠술포네이트 또는 P－톨루엔 술포네이트와 같은 치환이릴인 이탈기, 또는 히드록시이다), O2SF, 아세톡시 및 2,4－디니트로 펜옥시이다]와 반응시켜서 다음 구조식(Ic)의 화합물,[여기서, A 및 m은 앞에서 정의한 바와 같다]를 얻고, 이 화합물을 1 당량의 염기를 함유하는 불활성 반응 용매 중에서 환원시키되, X가 히드록시이고 m이 1인 경우에는 산성 매질중에서 환원시키는 것이 특징인 다음 구조식(Id)의 2,5－디치환－4(3H)－피리미돈류,[여기서, A 및 m은 앞에서 정의한 바와 같다]의 제조 방법.
- 불활성 반응 용매 존재하에 실온 내지 환류 온도에서 다음 구조식의 화합물,[여기서, R8은 제1항에서 정의한 바와 같다]을 다음 구조식의 화합물,XCH2CH2CH2NH2[여기서, X는 제3항에서 정의한 이탈기 또는 히드록시이다]과 반응시켜서 다음 구조식(Ⅴ)의 화합물,[여기서, X는 앞에서 정의한 바와 같다]를 얻되, X가 히드록시기 이외의 기인 경우에는 화합물(Ⅴ)를 다음 구조식(Ⅳ)의 화합물,[여기서, R6, R7및 q는 랙1항에서 정의한 바와 같다]과 불활성 반응 용매 존재하에 실온 내지 용매의 환류 온도에서 바람직하게는 거의 등몰량의 염기 존재하에, 더욱 바람직하게는 수산화 테트라부틸 암모늄과 같은 상전이 촉매의 존재하에 반응시켜 Z가 NO2인 다음 구조식(Ig)의 화합물.[여기서, R6, R7및 q는 앞에서 정의한 바와 같다]같고, z는 NO2또는 NH2이다]를 얻고, 이 화합물에서 Z가 NH2인 화합물을 얻고자 하는 경우에는 Z가 NO2인 화합물(Iq)를 환원시키되, 화합물(Ⅴ)에서 X가 히드록시인 경우에는 구조식(Ⅴ)의 화합물을 구조식(Ⅳ)의 화합물과 반응시키기 전에 활성화제, 바람직하게는 염화티오닐 또는 톨루엔술폰산과 반응시켜서 히드록시기를 공지의 이탈기로 전화시키는 것이 특징인 2,5－디치환－4(3H)－피리미돈류의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US534,426 | 1983-09-21 | ||
| US06/534,426 US4772704A (en) | 1983-09-21 | 1983-09-21 | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| US534426 | 1983-09-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850002259A true KR850002259A (ko) | 1985-05-10 |
| KR900001198B1 KR900001198B1 (ko) | 1990-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019840005791A KR900001198B1 (ko) | 1983-09-21 | 1984-09-21 | 히스타민 h₂-섭수체 길항 작용을 가진 2,5-디치환-4(3h)-피리미돈류 및 그 제조방법 |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4772704A (ko) |
| JP (1) | JPH0643310B2 (ko) |
| KR (1) | KR900001198B1 (ko) |
| AR (2) | AR242385A1 (ko) |
| AT (1) | AT387965B (ko) |
| AU (1) | AU583479B2 (ko) |
| BE (1) | BE900652A (ko) |
| CA (1) | CA1260463A (ko) |
| CH (1) | CH665840A5 (ko) |
| CS (1) | CS249147B2 (ko) |
| CY (1) | CY1561A (ko) |
| DD (1) | DD226881A5 (ko) |
| DE (1) | DE3434578A1 (ko) |
| DK (1) | DK162987C (ko) |
| ES (4) | ES8607253A1 (ko) |
| FI (1) | FI83868C (ko) |
| FR (1) | FR2552082B1 (ko) |
| GB (1) | GB2146994B (ko) |
| GR (1) | GR80439B (ko) |
| HK (1) | HK73790A (ko) |
| HU (1) | HU193227B (ko) |
| IE (1) | IE58083B1 (ko) |
| IL (1) | IL72990A (ko) |
| IT (1) | IT1176739B (ko) |
| LU (1) | LU85550A1 (ko) |
| NL (1) | NL8402898A (ko) |
| NO (1) | NO161561C (ko) |
| NZ (1) | NZ209572A (ko) |
| OA (1) | OA07820A (ko) |
| PT (1) | PT79256B (ko) |
| SE (1) | SE463209B (ko) |
| SG (1) | SG60890G (ko) |
| YU (1) | YU45205B (ko) |
| ZA (1) | ZA847345B (ko) |
| ZM (1) | ZM4984A1 (ko) |
| ZW (1) | ZW16084A1 (ko) |
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| JP2873340B2 (ja) * | 1988-04-29 | 1999-03-24 | 武田薬品工業株式会社 | 抗生物質ｔａｎ―１０５７，その製造法および用途 |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IN151188B (ko) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| ES477520A1 (es) * | 1978-02-25 | 1979-06-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevas penicilinas. |
| AU527202B2 (en) * | 1978-04-11 | 1983-02-24 | Smith Kline & French Laboratories Limited | 2-aminopyrimidones |
| US4496567A (en) * | 1978-11-13 | 1985-01-29 | Smith Kline & French Laboratories Limited | Phenyl alkylaminopyrimidones |
| US4521418A (en) * | 1979-02-21 | 1985-06-04 | Smith Kline & French Laboratories Limited | Guanidinothiazolyl derivatives |
| AU531142B2 (en) * | 1979-04-04 | 1983-08-11 | Smith Kline & French Laboratories Limited | 2 amino- pyimindones |
| CA1140129A (en) * | 1979-08-21 | 1983-01-25 | Ronald J. King | 4-pyrimidone derivatives |
| ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
| US4352933A (en) * | 1981-02-06 | 1982-10-05 | Smithkline Beckman Corporation | Chemical methods and intermediates for preparing substituted pyrimidinones |
| CA1206151A (en) * | 1981-12-28 | 1986-06-17 | Richard P. Pioch | Pyrimidone anti-ulcer agents |
| US4468399A (en) * | 1981-12-28 | 1984-08-28 | Eli Lilly And Company | 2-[2-(2-Aminoalkyl-4-thiazolylmethylthio)alkyl]-amino-5-substituted-4-pyrimidones |
| GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
| CA1275097A (en) * | 1984-10-02 | 1990-10-09 | Fujio Nohara | Pyridyloxy derivatives |
-
1983
- 1983-09-21 US US06/534,426 patent/US4772704A/en not_active Expired - Fee Related
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1984
- 1984-09-17 NZ NZ209572A patent/NZ209572A/en unknown
- 1984-09-18 FI FI843643A patent/FI83868C/fi not_active IP Right Cessation
- 1984-09-18 ZA ZA847345A patent/ZA847345B/xx unknown
- 1984-09-18 IL IL72990A patent/IL72990A/xx not_active IP Right Cessation
- 1984-09-18 ZW ZW160/84A patent/ZW16084A1/xx unknown
- 1984-09-18 ZM ZM49/84A patent/ZM4984A1/xx unknown
- 1984-09-19 NO NO843726A patent/NO161561C/no unknown
- 1984-09-19 CA CA000463533A patent/CA1260463A/en not_active Expired
- 1984-09-19 ES ES536054A patent/ES8607253A1/es not_active Expired
- 1984-09-19 YU YU1613/84A patent/YU45205B/xx unknown
- 1984-09-20 IT IT22744/84A patent/IT1176739B/it active
- 1984-09-20 JP JP59195868A patent/JPH0643310B2/ja not_active Expired - Lifetime
- 1984-09-20 GB GB08423863A patent/GB2146994B/en not_active Expired
- 1984-09-20 HU HU843539A patent/HU193227B/hu not_active IP Right Cessation
- 1984-09-20 DK DK450484A patent/DK162987C/da active
- 1984-09-20 AU AU33351/84A patent/AU583479B2/en not_active Ceased
- 1984-09-20 SE SE8404729A patent/SE463209B/sv not_active IP Right Cessation
- 1984-09-20 CH CH4510/84A patent/CH665840A5/de not_active IP Right Cessation
- 1984-09-20 FR FR8414463A patent/FR2552082B1/fr not_active Expired
- 1984-09-20 DE DE19843434578 patent/DE3434578A1/de not_active Withdrawn
- 1984-09-20 CS CS847103A patent/CS249147B2/cs unknown
- 1984-09-20 OA OA58396A patent/OA07820A/xx unknown
- 1984-09-20 IE IE240684A patent/IE58083B1/en not_active IP Right Cessation
- 1984-09-21 LU LU85550A patent/LU85550A1/fr unknown
- 1984-09-21 KR KR1019840005791A patent/KR900001198B1/ko not_active IP Right Cessation
- 1984-09-21 AR AR84298041A patent/AR242385A1/es active
- 1984-09-21 AT AT0300984A patent/AT387965B/de not_active IP Right Cessation
- 1984-09-21 DD DD84267496A patent/DD226881A5/de not_active IP Right Cessation
- 1984-09-21 PT PT79256A patent/PT79256B/pt not_active IP Right Cessation
- 1984-09-21 GR GR80439A patent/GR80439B/el unknown
- 1984-09-21 NL NL8402898A patent/NL8402898A/nl not_active Application Discontinuation
- 1984-09-21 BE BE0/213705A patent/BE900652A/fr not_active IP Right Cessation
-
1985
- 1985-06-14 ES ES544213A patent/ES8704465A1/es not_active Expired
-
1986
- 1986-01-31 ES ES551500A patent/ES8704155A1/es not_active Expired
- 1986-01-31 ES ES551501A patent/ES8702897A1/es not_active Expired
-
1987
- 1987-09-18 AR AR87308766A patent/AR242789A1/es active
-
1990
- 1990-07-21 SG SG608/90A patent/SG60890G/en unknown
- 1990-09-20 HK HK737/90A patent/HK73790A/xx unknown
-
1991
- 1991-03-22 CY CY1561A patent/CY1561A/xx unknown
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