KR890009899A - 신규의 2-구아니디노-티아졸 화합물 및 그의 제조방법과 파모티딘 제조시 중간체로서의 용도 - Google Patents
신규의 2-구아니디노-티아졸 화합물 및 그의 제조방법과 파모티딘 제조시 중간체로서의 용도 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims 4
- 150000008327 2-guanidinothiazoles Chemical class 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- -1 methoxyl group Chemical group 0.000 claims 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- GJTUPTFBMJUOAW-UHFFFAOYSA-N [SiH3]NS(=O)(=O)N Chemical class [SiH3]NS(=O)(=O)N GJTUPTFBMJUOAW-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
- GVFUPCFXJXOPNK-UHFFFAOYSA-N 1,1-dioxo-2-trimethylsilyl-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=O)(=O)N([Si](C)(C)C)C(=O)C2=C1 GVFUPCFXJXOPNK-UHFFFAOYSA-N 0.000 claims 1
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 claims 1
- TVXZVSURSGUYCJ-UHFFFAOYSA-N 2-[4-(1-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound N(C(=N)N)C=1SC=C(N1)CSC(C#N)C TVXZVSURSGUYCJ-UHFFFAOYSA-N 0.000 claims 1
- AHNNULCXEIGUHA-UHFFFAOYSA-N 2-[4-(sulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(N)=NC1=NC(CS)=CS1 AHNNULCXEIGUHA-UHFFFAOYSA-N 0.000 claims 1
- ZRAPHEBMDYQXKR-UHFFFAOYSA-N 2-trimethylsilylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N([Si](C)(C)C)C(=O)C2=C1 ZRAPHEBMDYQXKR-UHFFFAOYSA-N 0.000 claims 1
- AUKCYOUETBBMFV-UHFFFAOYSA-N 3-trimethylsilyl-1,3-oxazolidin-2-one Chemical compound C[Si](C)(C)N1CCOC1=O AUKCYOUETBBMFV-UHFFFAOYSA-N 0.000 claims 1
- JRRCIQNZZMKHMQ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-yl(trimethyl)silane Chemical compound C[Si](C)(C)N1CCN=C1 JRRCIQNZZMKHMQ-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- AYDOWLQVELNYEE-UHFFFAOYSA-N [dimethyl-(sulfamoylamino)silyl]methane Chemical compound C[Si](C)(C)NS(N)(=O)=O AYDOWLQVELNYEE-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ACTAPAGNZPZLEF-UHFFFAOYSA-N chloro(tripropyl)silane Chemical compound CCC[Si](Cl)(CCC)CCC ACTAPAGNZPZLEF-UHFFFAOYSA-N 0.000 claims 1
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 claims 1
- UKPGCPIEUXKREW-UHFFFAOYSA-N dichloromethane;n,n-dimethylacetamide Chemical compound ClCCl.CN(C)C(C)=O UKPGCPIEUXKREW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000002541 isothioureas Chemical class 0.000 claims 1
- LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 claims 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 239000005051 trimethylchlorosilane Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07D277/28—Radicals substituted by nitrogen atoms
-
- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- (a) 다음 일반식(Ⅰ)의 신규 화합물을 아크릴로니트릴과 반응시켜 3-(2-아니디노-티아졸-4-일-메틸티오)프로피오니트릴을 제조하고,위 식에서, R°는 수소원자 또는 C1-C5알킬기이고, m은 2-7이고, n은 2-4이며, (b) 다음 일반식(Ⅱ)의 신규 히드록소늄염을 3-치환-프로피오니트릴유도체와 8-20시간동안 반응시켜 다음 일반식(Ⅲ)의 화합물을 제조하며,위 식에서, R1은 수소원자, 메틸, 에틸 또는 페닐이고, O는 1-2이며, P는 2-3이고, X는 염소 또는 브롬이온, 메탄술포네이트 또는 트리프로오로메탄술포네이트이며, R°는 위에서 정의한 것과 같고 Z는 할로겐원자이며, 위의 반응에서, 메탄올의 존재하에서는 Z가 메톡실기인 상기 일반식(Ⅲ)의 화합물이 얻어지며, 암모니아 또는 염화암모늄과 반응시키면 Z가 아미노기인 일반식(Ⅲ)의 화합물이 얻어지고, 이들 화합물은 일반식(Ⅱ)에서 X로 표시되는 산부가염의 형태로 얻으며, (c) 상기 일반식(Ⅲ)의 화합물을 N-실릴아민, N-실릴아미드, N-실릴술파미드 또는 C1-C4알킬기를 가진 할로실란에서 선택된 실릴화제와 반응시켜 다음 일반식(Ⅳ)의 신규 실릴-화합물을 제조하여,(d) 상기 일반식(Ⅲ) 또는 (Ⅳ)의 화합물을 20-60℃의 온도에서 다음 일반식(Ⅵ)의 술파미드와 반응시켜서 다음 일반식(Ⅴ)의 신규의 실릴 화합물을 제조하고,상기 각 식에서, R°와 R은 위에서 정의한 것과 같고, R3는 수소원자, R(CH3)2Si 또는 C1-C4알킬실릴기이며, (e) 상기 일반식 (Ⅴ)에서 R°가 수소원자인 실릴화합물을 실온에서 직쇄 또는 측쇄형인 C1-C5알코올과 반응시켜서 파모티딘을 얻는 것을 특징으로 하는 2-구아니디노티아졸의 화합물을 제조하는 방법.
- 제1항에 있어서, N-메틸이소티오우레아, 아미디노이소티오우레아 또는 크산테이트 및 이소티오우레아의 S-(2-구아니디노-티아졸-4-일-메틸)유도체중에서 선택한 화합물을 실온에서 아세토니트릴, 이소프로판을 또는 그의 혼합물로부터 선택된 용매중에서 1당량의 물, 무기염기로서 수산화나트륨 수산화칼륨, 유기염기로서 트리에틸아민, 디에틸아민, 또는 비고리아미딘으로서 테트라메틸구아니딘 또는 펜타메틸구아니딘 또는 비시클릭아미딘과 반응시켜 R°이 수소원자인 일반식(Ⅰ)의 화합물을 제조하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 실온에서 아세토니트릴, 이소프로판을 또는 그의 혼합물로 부터 선택한 용매중에서 2-구아니디노-4-매르캅토메틸-티아졸을 1당량의 비시클릭아미딘과 반응시켜 R°이 수소원자인 일반식(Ⅰ)의 화합물을 제조하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅰ)의 화합물의 염을 아미딘 1,8-디아자비시클로[5.4.0운데트-7-엔 및 1,5-디아자비시클로[4.3.0]논-5-엔의 염증에서 선택하는 것을 특징으로하는 방법.
- 제1항에 있어서, 디옥산을 염화수소나 브롬화수소와 반응시켜 얻어지는 R이 수소원자, O가 1, P는 3 또는 O와 P가 2인 일반식(Ⅱ)의 히드록소늄염을 1,3-디옥산이나, 1,4-디옥산중에서 선택하여 20-30%의 농도로 3-10℃ 6-20시간동안 히드록소늄염 : 프로피오니트릴의 몰비를 1:3 - 1:7로 하여 3-(2-구아니디노-티아졸-4-일-메틸티오)프로피오니트릴과 결합시켜 R°이 수소원자, Z가 염소 또는 브롬원자인 일반식(Ⅲ)의 화합물을 얻고 메탄올과 몰비를 1:4 - 1:7로 하여 메탄올과 반응시켜 Z가 메톡실기인 일반식(Ⅲ)의 화합물을 제조하는 것을 특징으로 하는 방법.
- 제1항에 있어서, R°이 수소원자인 일반식(Ⅲ)의 화합물 또는 술페이트, 메탄술페이트, 트리플루오로 메탄술포네이트, 클로리드 또는 브로미드중에서 선택한 그위 산부가염을 헥사메틸디실라잔, 3-트리메틸실릴-2-옥사졸리디논, 1,3-비스-트리메틸실릴우레아, N,O-비스-트리메틸실릴아세트아미드, N-트리메틸실릴아세트아미드. N-트리메틸실릴사카린, N-트리메틸실릴프탈이미드, N-트리메틸실실뷰렛, N-트리메틸실피롤, N-트리메틸실릴이미다졸린, 트리메틸클로로실란, 트리에틸클로로실란, 트리프로필클로로실란, 디메틸터부틸쿨로로실란, N,O-비스-트리메틸실릴술파메이트중에서 선택한 실릴화제와 반응시킴으로써, N-트리메틸실릴술파미드와 반응시켰을때 R이 C1-C4알킬기인 일반식(Ⅴ)의 화합물을 생성기키는 일반식(Ⅳ)의 실릴화합물 용액을 얻는 것을 특징으로 하는 방법.
- 제1항에 있어서, R°이 수소원자인 일반식(Ⅲ)의 화합물이나 그의 부가염을 바람직하게는 아세토니트릴, 디옥산, 디메틸 아세트아미드 디클로메탄 또는 클로로포름중에서 선택한 불활성 비히드록실 용매중에서 N,N'-비스-트리메틸실릴술파미드, N,N'-테트라키스-트리메틸실릴술파미드, N,'-비스-디메틸-터부틸실릴술파미드, N,N'-비스-트리에틸실릴슬파미드,N,N'-비스-트리프로필 실릴술파미드 중에서 선택한 일반식 Ⅵ의 화합물과 반응시켜 R°이 수소원자이고 R은 앞서 정의한바와 같은 일반식(Ⅴ)의 실릴화합물을 얻는 것을 특징으로 하는 방법.
- 제1항에 있어서, R°이 수소원자이고 R이 메틸기인 일반식(Ⅴ)의 화합물의 용액을 메탄올, 이소프로판을, 또는 n-부탄올 중에서 선택한 알코올과 반응시켜 파모티딘을 얻는 것을 특징으로 하는 방법.
- 신규의 2-구아니디노티아졸 화합물 및 그의 제조방법과 파모티딘 제조시 중간체로서의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8800205 | 1987-12-17 | ||
| SE8800205 | 1987-12-17 | ||
| ES8800205A ES2008962A6 (es) | 1987-12-17 | 1987-12-17 | Proceso para la preparacion de nuevos compuestos de 2-guanidinotiazol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890009899A true KR890009899A (ko) | 1989-08-04 |
| KR910002877B1 KR910002877B1 (ko) | 1991-05-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880006697A KR910002877B1 (ko) | 1987-12-17 | 1988-06-03 | 신규의 2-구아니디노-티아졸 화합물 및 그들의 제조방법 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0322335A1 (ko) |
| JP (1) | JPH01172378A (ko) |
| KR (1) | KR910002877B1 (ko) |
| CN (1) | CN1033521A (ko) |
| DK (1) | DK354188D0 (ko) |
| ES (1) | ES2008962A6 (ko) |
| FI (1) | FI884338A0 (ko) |
| IL (1) | IL86649A0 (ko) |
| IS (1) | IS3359A7 (ko) |
| NO (1) | NO882562D0 (ko) |
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| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| US5856500A (en) * | 1997-03-11 | 1999-01-05 | Albemarle Corporation | Synthesis of thiazole derivatives |
| US5731442A (en) * | 1997-03-11 | 1998-03-24 | Albemarle Corporation | Synthesis of thiazole derivatives |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| CA2426122A1 (en) * | 2002-05-02 | 2003-11-02 | M/S Tonira Pharma Limited | A process for the preparation of a combination of famotidine polymorphis a and b |
| SG171690A1 (en) | 2005-03-22 | 2011-06-29 | Harvard College | Treatment of protein degradation disorders |
| EP1991247B1 (en) | 2006-02-14 | 2015-10-14 | President and Fellows of Harvard College | Bifunctional histone deacetylase inhibitors |
| MX2008010462A (es) | 2006-02-14 | 2009-04-17 | Harvard College | Inhibidores de histona desacetilasa. |
| JP5497431B2 (ja) | 2006-05-03 | 2014-05-21 | プレジデント アンド フェローズ オブ ハーバード カレッジ | ヒストンデアセチラーゼおよびチューブリンデアセチラーゼ阻害剤 |
| CN101081839B (zh) * | 2006-06-02 | 2010-12-29 | 范敏华 | 一种法莫替丁原料的精制工艺 |
| US8440716B2 (en) | 2008-07-23 | 2013-05-14 | President And Fellows Of Harvard College | Deacetylase inhibitors and uses thereof |
| US8716344B2 (en) | 2009-08-11 | 2014-05-06 | President And Fellows Of Harvard College | Class- and isoform-specific HDAC inhibitors and uses thereof |
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| DK160611C (da) * | 1979-09-04 | 1991-09-16 | Bristol Myers Squibb Co | Analogifremgangsmaade til fremstilling af 3,4-disubstituerede 1,2,5-thiadiazol-1-oxider og -1,1-dioxider |
-
1987
- 1987-12-17 ES ES8800205A patent/ES2008962A6/es not_active Expired
-
1988
- 1988-03-23 EP EP88500031A patent/EP0322335A1/en not_active Withdrawn
- 1988-05-06 JP JP63110322A patent/JPH01172378A/ja active Pending
- 1988-06-03 KR KR1019880006697A patent/KR910002877B1/ko not_active IP Right Cessation
- 1988-06-07 IL IL86649A patent/IL86649A0/xx unknown
- 1988-06-10 NO NO882562A patent/NO882562D0/no unknown
- 1988-06-14 IS IS3359A patent/IS3359A7/is unknown
- 1988-06-27 DK DK354188A patent/DK354188D0/da not_active Application Discontinuation
- 1988-06-29 CN CN88104081A patent/CN1033521A/zh active Pending
- 1988-09-21 FI FI884338A patent/FI884338A0/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL86649A0 (en) | 1988-11-30 |
| ES2008962A6 (es) | 1989-08-16 |
| DK354188D0 (da) | 1988-06-27 |
| KR910002877B1 (ko) | 1991-05-09 |
| IS3359A7 (is) | 1989-02-15 |
| EP0322335A1 (en) | 1989-06-28 |
| JPH01172378A (ja) | 1989-07-07 |
| CN1033521A (zh) | 1989-06-28 |
| NO882562D0 (no) | 1988-06-10 |
| FI884338A0 (fi) | 1988-09-21 |
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