KR850000428A - 2-설파모일벤조 [b] 티오펜 유도체의 제조방법 - Google Patents
2-설파모일벤조 [b] 티오펜 유도체의 제조방법 Download PDFInfo
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- KR850000428A KR850000428A KR1019840003455A KR840003455A KR850000428A KR 850000428 A KR850000428 A KR 850000428A KR 1019840003455 A KR1019840003455 A KR 1019840003455A KR 840003455 A KR840003455 A KR 840003455A KR 850000428 A KR850000428 A KR 850000428A
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- Prior art keywords
- alkyl
- compound
- formula
- aryl
- sulfamoylbenzo
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- 238000000034 method Methods 0.000 title claims 5
- UZMQSZBTFGHLAH-UHFFFAOYSA-N 1-benzothiophene-2-sulfonamide Chemical class C1=CC=C2SC(S(=O)(=O)N)=CC2=C1 UZMQSZBTFGHLAH-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- -1 chloro, bromo, iodo Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- XRZYWSVMYHEQPN-UHFFFAOYSA-N 6-hydroxy-1-benzothiophene-2-sulfonamide Chemical compound C1=C(O)C=C2SC(S(=O)(=O)N)=CC2=C1 XRZYWSVMYHEQPN-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000002585 base Substances 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
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims 1
- JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims 1
- 229960003495 thiamine Drugs 0.000 claims 1
- 235000019157 thiamine Nutrition 0.000 claims 1
- 239000011721 thiamine Substances 0.000 claims 1
- 229930192474 thiophene Natural products 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- (a) R이 -OH인 일반식(I) 화합물을 제조하기 위해서는, 상응하는 메틸에테르를 가수분해시키고, (b) R이인 일반식(I)화합물을 제조하기 위해서는, 화합물를 R1-CO -X1으로 처리하여(여기에서 R1은 상기에서 정의한 바와 같고, X1은 클로로, 브로모, 요오도, -OCOR1, -OCO CH2CH(CH3)2또는 -OCON(C6H5)2임), (c) R이 R1O-CO-O인 일반식(I)의 화합물을 제조하기 위해서는, 화합물를 일반식 R1-OCOCI의 클로로포로메이트 또는 일반식 R1OCOO'R'의 비스-카보네이트로 처리하고, (d) R이 Rα 1-O-인 일반식(I)화합물을 제조하기 위해서는 화합물를 화합물 Rα 1로 처리하며(여기에서 X2는 할로, 메실레이트, 토실레이트 또는 벤젠 설포네이트임). (e) R이 Rα 1이면 일반식(I) 화합물을 제조하기 위해서는, 화합물를 암모니아로 처리함을 특징으로 하여 일반식(I)의 화합물 및 안과학적으로 또는 약학적으로 허용되는 그의 염을 제조하는 방법.상기식에서, X는 수소, 클로로, 브로모 또는 플루오로와 같은 할로, C1-3알킬, 하이드록시 또는 C1-3알톡시이고 R은; 1) 하이드록시, 2) Rα 1[여기에서 Rα 1은 a) 한개 이상의 i) C3-6사이클로알킬 ii) 할로 iii) 아릴(여기에서 아릴 그룹은 카보사이클릭, 또는 헤테로사이클릭이고, 한개 이상의 C1-10알킬, 할로, C1-4알톡시, C2-5알카노일, 또는 트리플루오로 메틸로 치환될 수 있음). iv) 하이드록시, v) C1-3알톡시, vi) 아릴-C1-3알톡시, vii) C1-4알톡시-C1-3알톡시, viii) 아미노, ix)(C1-3알킬)아미노, x) 디(C-3알킬)아미노, xi)(여기에서 R2는 1) H0-, 2) M+0-(여기에서 M+는 약학적으로 허용되는 양이온임). 3) C1-10알톡시, 4) R3R4N- (여기에서 R3및 R4는 독립적으로 수소, 하이드록시, C1-15알킬이거나, 또는 R3및 R4가 이들이 결합하고 있는 질소와 함께 3 내지 7원 헤테로사이클을 형성함)이고, 또는 xii) C2-5알카노일로 치환된 C1-18알킬의 직쇄 또는 분지쇄 b) C3-6사이클로알킬 c) C1-18알킬-C3-6사이클로알킬 d) 상기에서 정의한 바와 같은 아릴 e) R3R4N- f) C2-6알케닐, g) 아릴-C2-6알케닐, h) C2-6알키닐, 또는 i) 0, N 및 S중에서 선택된 한개 또는 2개의 이종원자를 갖는 5 또는 6원의 헤테로 사이클임].3)(여기에서 R1은 Rα 1또는 C1-18알킬임). 5)7)(여기에서 x는 0 내지 2이고 V는 0 내지 3이며, Z는 0 또는 1이고 A는 S, O 및 N중에서 선택된 이종원자임).8)[여기에서 R5와 R6는 독립적으로 a) 수소, b) C1-18알킬의 직쇄 또는 분지쇄, c) C3-6사이클로알킬, d) C3-6사이클로알킬-C1-3알킬, e) 아릴-C|1-3알킬(여기에서, 아릴 그룹은 비치환된 또는 한개 이상의 클로르, 브로모, 플루오로, C1-3알킬 또는 C1-3알톡시로 치환됨).f)(여기에서 R7은 i) C1-18알킬의 직쇄 또는 분지쇄, ii) 비치환된 또는 한개 이상의 클로르, 브로모, 플루오로, C1-3알킬, 또는 C1-3알톡시로 치환된 아릴, iii) 아릴-C1-3알킬(여기에서 아릴그룹은 비치환 되거나 한개 이상의 클로로, 브로모, 플루오로, C1-3알킬 또는 C1-3알톡시로 치환됨).iv) 아미노-C1-8알킬의 직쇄 또는 분지쇄임), 또는 g) 저급알킬(이때는 R5와 R6가 직접 또는 0 또는 N중에서 선택된 이종원자를 통해 결합되어 그들이 함께 결합하고 있는 질소를 5 또는 6원의 헤테로사이클을 형성함)이다].9) M+0- (여기에서 M+는 나트륨, 칼륨, 암모늄, 4급(C1-4알킬)암모늄, 피리디늄, 이미다졸륨, 프롤리독심 및 티아민 중에서 선택된 안과학적으로 허용되는 양이온 임).10)(여기에서 M+는 상기에서 정의한 바와 같음).11)(여기에서 R80C1-3알킬 또는 페닐 -C1-3알킬임), 또는12)(여기에서 R8은 전술한 바와 같고, 2개가 같거나 다를 수 있음)이고, R과 X는 함께 결합되어 메틸닐디옥시를 나타낸다.
- 제1항에 있어서, R이 제5 또는 6위치인 화합물의 제조방법.
- 제2항에 있어서, X가 수소이고 R이 HO-,또는 R5R6N- 인 화합물의 제조방법.
- 제3항에 있어서, R'이 C1-4알킬인 화합물의 제조방법.
- 제3항에 있어서, 5(또는 6)-하이드록시-2-설파모일벤조 [b] 티오펜, 5(또는 6)-(2-설파모일벤조[b] 티에닐)아세테이트, 5(또는 6)-(2-설파모일벤조 [b] 티에닐)2,2-디메틸프로피오네이트, 5(또는 6) -(2-설파모일벤조 [b] 티에닐) 2-메틸프로피오네이트, 또는 5(또는 6)-(2-설파모일벤조 [b] 티에닐) 3-메톡시-카보닐프로피오네이트의 제조방법.
- 제3항에 있어서 6-하이드록시-2-설파모일벤조 [b] 티오펜의 제조방법.
- a) 구조식의 화합물을 환원시키고, b) 구조식의 화합물을 산화시키며, c) 일반식(여기에서, 할로는 Cl, Br 또는 I임)의 화합물을 탈할로겐화 시키고, d) 구조식의 화합물을 아미노화 시키며, e) 일반식(여기에서 M은 알카리 금속 양이온임)의 화합물을 친전자성 질소 화합물로 처리하고, f) 일반식의 화합물을 산 또는 염기로 처리하며, g)구조식의 화합물을 이산화황액중에서 무수 할로겐화 수소로 처리하고 h) 구조식의 화합물을 디아조화시키며 i) 일반식(여기에서 R9은 수소, C1-4알킬, 페닐-C1-4알킬 또는 페닐임)의 화합물을 암모니아 또는 암모늄 이온으로 처리하고, j)일반식(여기에서 R10은 C1-4알킬, 또는 페닐-C1-4알킬임)의 화합물을 탈에테르화 시키고, k) 일반식의 화합물을 탈아실화시키며, l) 구조식의 화합물을 환원시킴을 특징으로 하여 구조식의 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50609283A | 1983-06-20 | 1983-06-20 | |
| US506,092 | 1983-06-20 | ||
| US506092 | 1983-06-20 | ||
| US54719183A | 1983-10-31 | 1983-10-31 | |
| US547191 | 1983-10-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850000428A true KR850000428A (ko) | 1985-02-27 |
| KR890000386B1 KR890000386B1 (ko) | 1989-03-16 |
Family
ID=27055356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840003455A KR890000386B1 (ko) | 1983-06-20 | 1984-06-19 | 2-설파모일벤조[b]티오펜 유도체 및 이의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0129478B1 (ko) |
| KR (1) | KR890000386B1 (ko) |
| AU (1) | AU558665B2 (ko) |
| CA (1) | CA1253151A (ko) |
| DE (1) | DE3481057D1 (ko) |
| DK (1) | DK298584A (ko) |
| ES (1) | ES8600272A1 (ko) |
| FI (1) | FI80032C (ko) |
| GR (1) | GR82372B (ko) |
| HU (1) | HUT37420A (ko) |
| IE (1) | IE57601B1 (ko) |
| IL (1) | IL72070A (ko) |
| NO (1) | NO842467L (ko) |
| NZ (1) | NZ208444A (ko) |
| PT (1) | PT78762A (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820848A (en) * | 1984-12-12 | 1989-04-11 | Merck & Co., Inc. | Substituted aromatic sulfonamides as antiglaucoma agents |
| DE3568431D1 (en) * | 1984-12-12 | 1989-04-06 | Merck & Co Inc | Substituted aromatic sulfonamides, their preparation and ophthalmic compositions containing them |
| US4731368A (en) * | 1986-12-08 | 1988-03-15 | Merck & Co., Inc. | Thienopyridine sulfonamides and their ophthalmological formulation |
| EP0271273A3 (en) * | 1986-12-08 | 1989-07-12 | Merck & Co. Inc. | Thieno-and furopyridine sulfonamides |
| US4808595A (en) * | 1986-12-24 | 1989-02-28 | Merck & Co., Inc. | Furopyridine sulfonamides and their opthalmological compositions |
| US4894390A (en) * | 1987-08-03 | 1990-01-16 | Merck & Co., Inc. | Substituted thieno[2,3-b]thiophene-2-sulfonamides as antiglaucoma agents |
| CA1320487C (en) * | 1987-08-03 | 1993-07-20 | George D. Hartman | Substituted thieno[2,3-.beta.]thiophene-2-sulfonamides as antiglaucoma agents |
| US4751231A (en) * | 1987-09-16 | 1988-06-14 | Merck & Co., Inc. | Substituted thieno[2,3-b]pyrrole-5-sulfonamides as antiglaucoma agents |
| US4929549A (en) * | 1989-02-08 | 1990-05-29 | Merck & Co., Inc. | 5-carbamoylthieno[2,3-b]thiophene-2-sulfon-amides as topically active carbonic anhydrase inhibitors |
| AU3378399A (en) * | 1998-04-02 | 1999-10-25 | Ortho-Mcneil Pharmaceutical, Inc. | 4-thionaphthyl-1h-imidazoles with alpha-2-adrenergic activity |
| US6313309B1 (en) * | 1999-04-05 | 2001-11-06 | Ortho-Mcneil Pharmaceutical, Inc. | 4-thionaphthyl—1H—imidazoles which are usefulα22-adrenoceptoR agonists/ antagonists |
| SI2348022T1 (sl) | 2005-03-28 | 2013-05-31 | Toyama Chemical Co., Ltd. | Postopek proizvodnje 1-(3-(2-(1-benzotiofen-5-il)etoksi)propil)azetidin-3-ola ali soli le-tega |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR241136A1 (es) * | 1981-07-13 | 1991-11-29 | Merck E Co Inc | Procedimiento para preparar esteres de 6-hidroxi-2-benzotiazolsulfonamida para tratamiento topicode presion intraocular elevada" |
| US4386098A (en) * | 1981-11-03 | 1983-05-31 | Merck & Co., Inc. | 6-Hydroxy-2-benzothiazolesulfonamide for the topical treatment of elevated intraocular pressure |
| US4426388A (en) * | 1982-04-02 | 1984-01-17 | Merck & Co., Inc. | 5-Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
-
1984
- 1984-06-11 NZ NZ208444A patent/NZ208444A/en unknown
- 1984-06-11 IL IL72070A patent/IL72070A/xx not_active IP Right Cessation
- 1984-06-13 ES ES533390A patent/ES8600272A1/es not_active Expired
- 1984-06-14 DE DE8484401227T patent/DE3481057D1/de not_active Expired - Fee Related
- 1984-06-14 GR GR75021A patent/GR82372B/el unknown
- 1984-06-14 EP EP84401227A patent/EP0129478B1/en not_active Expired - Lifetime
- 1984-06-18 CA CA000456789A patent/CA1253151A/en not_active Expired
- 1984-06-18 PT PT78762A patent/PT78762A/pt not_active IP Right Cessation
- 1984-06-19 IE IE1536/84A patent/IE57601B1/en not_active IP Right Cessation
- 1984-06-19 DK DK298584A patent/DK298584A/da not_active Application Discontinuation
- 1984-06-19 AU AU29496/84A patent/AU558665B2/en not_active Ceased
- 1984-06-19 KR KR1019840003455A patent/KR890000386B1/ko not_active IP Right Cessation
- 1984-06-19 FI FI842478A patent/FI80032C/fi not_active IP Right Cessation
- 1984-06-19 HU HU842363A patent/HUT37420A/hu unknown
- 1984-06-19 NO NO842467A patent/NO842467L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES533390A0 (es) | 1985-10-01 |
| HUT37420A (en) | 1985-12-28 |
| IE57601B1 (en) | 1993-01-27 |
| AU2949684A (en) | 1985-06-13 |
| FI842478A (fi) | 1984-12-21 |
| DE3481057D1 (de) | 1990-02-22 |
| IL72070A0 (en) | 1984-10-31 |
| IL72070A (en) | 1988-11-30 |
| FI80032B (fi) | 1989-12-29 |
| EP0129478A3 (en) | 1987-03-25 |
| CA1253151A (en) | 1989-04-25 |
| FI842478A0 (fi) | 1984-06-19 |
| KR890000386B1 (ko) | 1989-03-16 |
| PT78762A (en) | 1984-07-01 |
| GR82372B (ko) | 1984-12-13 |
| EP0129478A2 (en) | 1984-12-27 |
| IE841536L (en) | 1984-12-20 |
| DK298584A (da) | 1984-12-21 |
| EP0129478B1 (en) | 1990-01-17 |
| AU558665B2 (en) | 1987-02-05 |
| ES8600272A1 (es) | 1985-10-01 |
| DK298584D0 (da) | 1984-06-19 |
| NO842467L (no) | 1985-12-21 |
| NZ208444A (en) | 1987-08-31 |
| FI80032C (fi) | 1990-04-10 |
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