KR910011813A - 2-치환된 4-(3-알킬-5-3급-부틸-4-하이드록시페닐) 티아졸, 이의 제조방법, 이를 함유하는 약제 및 이의 용도 - Google Patents
2-치환된 4-(3-알킬-5-3급-부틸-4-하이드록시페닐) 티아졸, 이의 제조방법, 이를 함유하는 약제 및 이의 용도 Download PDFInfo
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- KR910011813A KR910011813A KR1019900020441A KR900020441A KR910011813A KR 910011813 A KR910011813 A KR 910011813A KR 1019900020441 A KR1019900020441 A KR 1019900020441A KR 900020441 A KR900020441 A KR 900020441A KR 910011813 A KR910011813 A KR 910011813A
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- 239000003814 drug Substances 0.000 title claims 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- -1 alkyl radical Chemical class 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- JNHDLNXNYPLBMJ-UHFFFAOYSA-N 1,3-thiazol-2-ylmethanol Chemical compound OCC1=NC=CS1 JNHDLNXNYPLBMJ-UHFFFAOYSA-N 0.000 claims 1
- RPROPEJMPWCKPG-UHFFFAOYSA-N 3-[4-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]propanoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2N=C(CCC(O)=O)SC=2)=C1 RPROPEJMPWCKPG-UHFFFAOYSA-N 0.000 claims 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- 235000021342 arachidonic 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000006772 olefination reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
- C07D417/02—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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07—ORGANIC CHEMISTRY
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—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
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- Lubricants (AREA)
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Abstract
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Description
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Claims (11)
- 일반식(I)의 2-치환된 4-(3-알킬-5-3급-부틸-4-하이드록시페닐)티아졸 및 이의 생리학적으로 허용되는 염(X가 하이드록실 또는 하이드록시아미노 그룹일 경우),상기식에서, R1은 포화되거나 불포화된 직쇄 또는 측쇄 C1-C5알킬그룹이고, R2는 수소 또는 탄소수 1 내지 3의 알킬 라디칼이며, A는 일반식 -(CH2)n-Y-CR3R4-; -CH=CR3-(CH2)m- 또는 -CH=N-O-(CH2)n-(여기에서, Y는 단일결합, 산소 또는 황원자이거나 카보닐 그룹이고 R3및 R4는 동일하거나 상이하고 수소 또는 탄소수 2이하의 알킬라디칼이며 m은 0 내지 3이며 n은 1 내지 4이다)의 중간체 쇄이며, Z는 테트라졸 또는 CN그룹이거나 일반식(여기에서, X는 하이드록실 그룹 또는 일반식 R5O- 또는 R6R7N-라디칼이고 R5는 하이드록실, C1-C3-알콕시 또는 C1-C3-알킬아미노에의해 임의로 치환된 직쇄 또는 측쇄 C1-C4-알킬 라디칼이며, R6및 R7은 동일하거나 상이하며, 수소, 직쇄 또는 측쇄 C1-C6알킬 라디칼이거나 R6가 수소 또는 C1-C4-알킬 라디칼인 경우 R7은 하이드록실, C1-C3-알콕시 또는 테트라졸-5-일 그룹이거나, X는 구조성분-A-(C=O)-와 함께 일반식라디칼이고 R8은 수소, C1-C3알킬라디칼 또는 C1-C3알콕시라디칼이다)의 라디칼이다.
- 제1항에 있어서, R1이 3급-부틸 또는 메틸그룹이고 R2가 수소 또는 메틸이며 A가 일반식 -(CH2)n-Y-CR3R4- (여기에서 Y는 단일결합 또는 산소원자이고 R3및 R4는 동일하거나 상이하고 수소 또는 메틸 라디칼이며 n은 1또는 2이다)의 중간체 쇄이며 X가 하이드록실 그룹 또는 일반식 R5O- 또는 R6R7N- (여기에서, R5는 직쇄 또는 측쇄 C1-C3알킬 라디칼이고 R6은 수소 또는 메틸 라디칼이며 R7은 하이드록실, 메톡시 또는 테트라졸-5-일 그룹이다)의 라디칼인 일반식(I)의 화합물.
- 제2항에 있어서, R1이 3급-부틸 그룹이고 R2가 수소 또는 메틸이며 A가 일반식 -(CH2)n-Y-CR3R4- (여기에서 Y는 단일결합이고 R3및 R4는 수소이며 n은 1또는 2이다)의 중간체 쇄이며 X가 하이드록실 그룹 또는 일반식 R6R7N라디칼 (여기에서, R5는 수소 또는 메틸 라디칼이고 R7은 하이드록실, 메톡시 그룹이다)인 일반식(I)의 화합물.
- 제3항에 있어서, 3-[4-(3,5-디-3급-부틸-4-하이드록시페닐)티아졸-2-일]프로피온산인 화합물.
- a)일반식(Ⅲ)의 티아카복사미드를 일반식(Ⅳ)의 2-할로-1-페닐알카논과 반응시켜 본 발명에 따른 일반식(Ia)의 화합물을 수득하거나, b)일반식(Ⅴ)의 티아졸 알데히드를 일반식(Ⅵ)의 디알킬 포스포네이트와 올레핀화 반응시켜 본 발명에 따른 일반식(Ib)의 알케노산 에스테르를 수득하거나, c) b)의 올레핀화 반응에서 전술한 일반식(Ⅴ)의 티아졸 알데히드 중 하나를 강염기의 존재하에 일반식(Ⅶ)의 할로피롤리디논 및 포스핀산 또는 포스포르산 에스테르와 올레핀화 반응시켜 본 발명에 따른 일반식(Ic)의 화합물을 수득하거나, d)일반식(Ⅴ)의 화합물을 일반식(Ⅷ)의 하이드록실 아민과 축합시켜 본 발명에 따른 일반식(Id)의 화합물을 수득하거나, e)일반식(Ⅸ)의 하이드록시메틸티아졸을 출발물질로 사용하여 트리-또는 테트라할로겐화 알칸 및 강염기의 존재하에 일반식 R3-CO-R4(여기에서, R1, R2및 R4는 제1항에서, 정의한 바와 같다)의 케톤과 반응시켜 본발명에 따른 일반식(Ie)의 화합물을 수득하거나, f)바람직하게는 X가 R5O인 일반식(Ia), (Ib) 및 (Ic) 의 화합물을 염기 존재하에 가수분해시켜 X가 OH인 일반식 (I)의 화합물을 수득하거나, g)X가 OH인 일반식(Ⅰ)의 화합물을 축합제 또는 활성화된 유도체의 존재하에 알콜R5OH, 아민 또는 하이드록실아민 R6R7NH를 사용하여 X가 R5O 또는 R6R7N(여기에서 R5, R6및 R7은 제1항에서 정의한 바와 같다)그룹인 일반식(I)의 화합물로 전환시키거나, h)X가 R5O 라디칼인 일반식(I)의 화합물을 염기 R5R6NH를 사용하여 X가 R6R7N그룹인 일반식 (I)의 아미드로 전환시키거나, i)본 발명에 따른 일반식(Ib)의 화합물의 촉매적 수소화에 의하여 R1,R2및 R5가 제1항에서 정의한 바와 같고 R3가 수소 또는 메틸이 R4가 수소이고, Y가 단일 결합인 일반식(Ia)의 화합물을 제조함을 특징으로하여, 제1항 내지 제4항중 어느 한항에 따른 일반식(I)의 2-치환된 4-(3-3급-부틸-4-하이드록시페닐)티아졸 및 필요하다면 이의 생리학적으로 허용되는 염을 제조하는 방법.상기식에서, R1,R2,R3,R4,R5R8,Y,m,n,Z 및 X는 제1항에서 정의한 바와 같고, W는 할로겐, 바람직하게는 염소 또는 브롬이며, R9는 C1-C3-알킬 라디칼이다.
- 약제로서 사용하기 위한, 제5항에 따른 방법으로 수득한 제1항 내지 4항중 어느 한항에 따른 일반식(I)의 화합물 및 필요하다면 이의 생리학적으로 허용되는 염.
- 제1항 내지 4항중 어느 한항에 따른 적어도 하나의 일반식(I)의 화합물 및/또는 적어도 하나의 이의 생리학적으로 허용되는 염 및/또는 제5항에 따른 방법으로 제조된 적어도 하나의 화합물을 함유하거나 이들로 이루어진 약제.
- 제7항에 있어서, 염증 억제제, 면역조절제, 산소 유리라디칼 탈활성화제 및/또는 5-리폭시게나제 및/또는 사이클로옥시게나제에 의해 중개된 아라키돈산 분해의 억제제의 치료적 투여가 지시된 질환의 예방 및 치료를 위한 약제.
- 제7항 또는 8항에 있어서, 염증성 질환, 특히 염증성 류마티스 질환의 예방 및 치료에 사용되는 약제.
- 적어도 하나의 일반식(Ⅰ)의 화합물 및/또는 적어도 하나의 이의 생리학적으로 허용되는 염 및/또는 제5항에 따른 방법으로 수득한 하나의 화합물을 생리학적으로 허용되는 담체 및 필요하다면 기타 부가제 및/또는 보조제와의 적합한 투여형으로 형성시킴으로써 제7항 내지 9항중 어느 한항에 따른 약제를 생산하는 방법.
- 제8항 및 9항에 따른 약제를 생산하기 위한, 일반식(I)의 화합물 및/또는 필요하다면 이의 생리학적으로 허용되는 염의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3941438A DE3941438A1 (de) | 1989-12-15 | 1989-12-15 | Neue 2-substituierte 4-(3-alkyl-5-tert.-butyl-4-hydroxy-phenyl)-thiazole, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung |
| DEP39414388 | 1989-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR910011813A true KR910011813A (ko) | 1991-08-07 |
Family
ID=6395527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900020441A KR910011813A (ko) | 1989-12-15 | 1990-12-13 | 2-치환된 4-(3-알킬-5-3급-부틸-4-하이드록시페닐) 티아졸, 이의 제조방법, 이를 함유하는 약제 및 이의 용도 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5137897A (ko) |
| EP (1) | EP0432740B1 (ko) |
| JP (1) | JPH0517459A (ko) |
| KR (1) | KR910011813A (ko) |
| AT (1) | ATE119527T1 (ko) |
| AU (1) | AU630261B2 (ko) |
| CA (1) | CA2032282A1 (ko) |
| DE (1) | DE3941438A1 (ko) |
| FI (1) | FI906141A (ko) |
| HU (1) | HU209584B (ko) |
| IE (1) | IE904515A1 (ko) |
| IL (1) | IL96659A0 (ko) |
| NO (1) | NO905411L (ko) |
| NZ (1) | NZ236453A (ko) |
| PT (1) | PT96181A (ko) |
| RU (2) | RU2017739C1 (ko) |
| ZA (1) | ZA9010067B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2600644B2 (ja) * | 1991-08-16 | 1997-04-16 | 藤沢薬品工業株式会社 | チアゾリルベンゾフラン誘導体 |
| EP0548017A1 (de) * | 1991-12-18 | 1993-06-23 | Ciba-Geigy Ag | Neue Thiazole |
| TW211005B (ko) * | 1991-12-18 | 1993-08-11 | Ciba Geigy Ag | |
| DE19502209A1 (de) * | 1995-01-25 | 1996-08-01 | Hoechst Ag | Phosphonoessigsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| FR2812546B1 (fr) * | 2000-08-01 | 2008-11-21 | Sod Conseils Rech Applic | Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments |
| TWI283577B (en) * | 1999-10-11 | 2007-07-11 | Sod Conseils Rech Applic | Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof |
| FR2799461B1 (fr) * | 1999-10-11 | 2002-01-04 | Sod Conseils Rech Applic | Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments |
| JP4917243B2 (ja) * | 2001-05-23 | 2012-04-18 | 日本曹達株式会社 | チアゾール化合物の製造方法 |
| US7521563B2 (en) * | 2004-08-10 | 2009-04-21 | Shizuoka Coffein Co., Ltd. | Hydroxamic acid derivative and medicine containing the same as active ingredient |
| EP1939181A1 (en) * | 2006-12-27 | 2008-07-02 | sanofi-aventis | Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase |
| CN114516824A (zh) * | 2022-03-18 | 2022-05-20 | 广州佳途科技股份有限公司 | 一种硫代酰胺羧酸酯及其合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130759C (ko) * | 1965-10-07 | |||
| US4636516A (en) * | 1981-02-19 | 1987-01-13 | Yamanouchi Pharmaceutical Co., Ltd. | 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds |
| US4535165A (en) * | 1981-11-23 | 1985-08-13 | Riker Laboratories, Inc. | Substituted diazoles and thiazoles |
| JPS62132871A (ja) * | 1985-12-03 | 1987-06-16 | Yamanouchi Pharmaceut Co Ltd | 新規チアゾ−ル誘導体 |
| DE3702758A1 (de) * | 1987-01-30 | 1988-09-29 | Hoechst Ag | Substituierte 3-phenyl-7h-thiazolo (3,2-b) (1,2,4) triazin-7-one, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung, sowie einige bei der herstellung der genannten verbindungen gebildete zwischenprodukte |
| GB8717068D0 (en) * | 1987-07-20 | 1987-08-26 | Fujisawa Pharmaceutical Co | Nitric ester derivative |
-
1989
- 1989-12-15 DE DE3941438A patent/DE3941438A1/de not_active Withdrawn
-
1990
- 1990-12-11 AT AT90123853T patent/ATE119527T1/de not_active IP Right Cessation
- 1990-12-11 EP EP90123853A patent/EP0432740B1/de not_active Expired - Lifetime
- 1990-12-13 RU SU904894048A patent/RU2017739C1/ru active
- 1990-12-13 HU HU908258A patent/HU209584B/hu not_active IP Right Cessation
- 1990-12-13 US US07/626,784 patent/US5137897A/en not_active Expired - Fee Related
- 1990-12-13 KR KR1019900020441A patent/KR910011813A/ko not_active Application Discontinuation
- 1990-12-13 RU SU904894274A patent/RU2021264C1/ru active
- 1990-12-13 FI FI906141A patent/FI906141A/fi not_active Application Discontinuation
- 1990-12-13 PT PT96181A patent/PT96181A/pt unknown
- 1990-12-13 IL IL96659A patent/IL96659A0/xx unknown
- 1990-12-13 NZ NZ236453A patent/NZ236453A/en unknown
- 1990-12-14 NO NO90905411A patent/NO905411L/no unknown
- 1990-12-14 AU AU68024/90A patent/AU630261B2/en not_active Ceased
- 1990-12-14 JP JP2419334A patent/JPH0517459A/ja active Pending
- 1990-12-14 ZA ZA9010067A patent/ZA9010067B/xx unknown
- 1990-12-14 IE IE451590A patent/IE904515A1/en unknown
- 1990-12-14 CA CA002032282A patent/CA2032282A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO905411L (no) | 1991-06-17 |
| PT96181A (pt) | 1991-09-30 |
| EP0432740A2 (de) | 1991-06-19 |
| ATE119527T1 (de) | 1995-03-15 |
| ZA9010067B (en) | 1991-09-25 |
| IL96659A0 (en) | 1991-09-16 |
| HU908258D0 (en) | 1991-06-28 |
| NO905411D0 (no) | 1990-12-14 |
| RU2017739C1 (ru) | 1994-08-15 |
| FI906141A0 (fi) | 1990-12-13 |
| EP0432740A3 (en) | 1992-01-02 |
| FI906141A (fi) | 1991-06-16 |
| CA2032282A1 (en) | 1991-06-16 |
| RU2021264C1 (ru) | 1994-10-15 |
| JPH0517459A (ja) | 1993-01-26 |
| AU6802490A (en) | 1991-06-20 |
| NZ236453A (en) | 1992-07-28 |
| IE904515A1 (en) | 1991-06-19 |
| HUT58306A (en) | 1992-02-28 |
| EP0432740B1 (de) | 1995-03-08 |
| US5137897A (en) | 1992-08-11 |
| DE3941438A1 (de) | 1991-06-20 |
| AU630261B2 (en) | 1992-10-22 |
| HU209584B (en) | 1994-08-29 |
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