KR960037634A - 항바이러스제 제조를 위한 중간물질 및 방법 - Google Patents
항바이러스제 제조를 위한 중간물질 및 방법 Download PDFInfo
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- KR960037634A KR960037634A KR1019960009829A KR19960009829A KR960037634A KR 960037634 A KR960037634 A KR 960037634A KR 1019960009829 A KR1019960009829 A KR 1019960009829A KR 19960009829 A KR19960009829 A KR 19960009829A KR 960037634 A KR960037634 A KR 960037634A
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- 238000000034 method Methods 0.000 title claims abstract 6
- 239000003443 antiviral agent Substances 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title 1
- -1 (1R, trans) propenyl 3-methylene-1,2-cyclopropanedimethanol Chemical compound 0.000 claims abstract 21
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims abstract 9
- 150000002009 diols Chemical class 0.000 claims abstract 9
- 150000002905 orthoesters Chemical class 0.000 claims abstract 2
- 230000003647 oxidation Effects 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- 239000011968 lewis acid catalyst Substances 0.000 claims 5
- 239000012285 osmium tetroxide Substances 0.000 claims 5
- 229910000489 osmium tetroxide Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 4
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 claims 4
- 125000002221 trityl group Chemical class [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 229910015900 BF3 Inorganic materials 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical group COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims 2
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical group NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 229940070891 pyridium Drugs 0.000 claims 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 claims 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims 1
- SWWZYFVOUUTMPJ-UHFFFAOYSA-N 2-(hydroxymethyl)cyclobutan-1-one Chemical compound OCC1CCC1=O SWWZYFVOUUTMPJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/39—Saturated compounds containing a keto group being part of a ring of a three- or four-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
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- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
본 발명은 (1R, 트랜스)이보호 3-메틸렌-1,2-시클로프로판디메탄올을 광학적 활성 디올 중간물질로 산화시킨 후, 오르토에스테르 중간물질로 고리화 반응시키고, (2S-트랜스)이보호 2,3-비스(히드록시메틸)시클로부탄온으로 전환시키는 방법에 관한 것이다. 이러한 시클로부탄온은 항바이러스제인 〔1R-(1α,2β,3α)〕-2-아미노-9-〔2,3-비스(히드록시메틸)시클로부틸〕-1,9-디히드로-6H-푸린-6-온을 제조함에 있어서 중간물질로서 유용하다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- a) 하기 일반식의 광학적 활성 3-메틸렌 화합물 :을 사산화오스뮴으로 산화시켜 하기 일반식의 광학적 활성 디올 :을 수득하는 단계 ; b) 상기 단계(a)의 디올 생성물을 약산 촉매의 존재하에 일반식 : R4-C-(O-R3)3(이때, R3은 메틸 또는 에틸이고, R4는 탄소수 1 내지 6개의 직쇄 또는 측쇄 알킬 또는 페닐임)의 트리메틸 또는 트리에틸 오르토에스테르로 처리함으로써 하기 일반식의 시클릭 오르토에스테르 :로 전환시키는 단계 ; 및 c) 상기 단계(b)로부터의 시클릭 오르토에스테르 생성물을 루이스산 촉매로 처리함으로써 목적하는 광학적 활성 시클로부탄온을 수득하는 단계를 포함하는 하기 일반식의 광학적 활성 시클로부탄온 :(이때, R1은 히드록시 보호기임)의 제조 방법.
- 제1항에 있어서, 단계(a)에서 사산화오스뮴이 보조 산화제로서 4-메틸모르폴린, N-산화물을 포함하므로써 촉매량으로 사용되고 ; 단계(b)에서 트리메틸 또는 티리에틸 오르토에스테르가 트리메틸 오르토아세테이트이며; 단계(b)에서 약산 촉매가 피리듐 p-톨루엔술포네이트이고 ; 및 단계(c)에서 루이스산 촉매가 에테르계 삼불화붕소, 트리메틸실릴 트리플루오로메탄술포네이트, 삼염화붕소, 삼브롬화붕소, 디에틸알루미늄 염화물, 에틸알루미늄 이염화물, 알루미늄 삼염화물, 사염화티탄, 사염화주석 또는 삼염화주석인 방법.
- 제2항에 있어서, 단계(c)에서 루이스산 촉매가 에테르계 삼불화붕소인 방법.
- a) 하기 일반식의 광학적 활성 3-메틸렌 화합물 :을 사산화오스뮴의 촉매량 및 보조 산화제로서 4-메틸모르폴린 N-신화물을 함유하는 수용액으로 산화하여 하기 일반식의 광학적 활성 디올 :을 수득하는 단계 ; b) 상기 단계(a)의 디올 생성물에 피리듐 p-톨루엔 술포네이트의 존재하에 트리메틸 오르토아세테이트를 처리함으로써 하기 일반식의 시클릭 오르토에스테르 :로 전환시키는 단계 ; c) 상기단계(b)의 시클릭 오르토에스테르 생성물에 에테르계 삼불화붕소를 처리함으로써 목적하는 광학적 활성 시클로부탄온을 수득하는 단계를 호함하는 하기 일반식의 광학적 활성 시클로부탄온 :의 제조 방법.
- a) 하기 일반식의 광학적 활성 3-메틸렌 화합물 :(이때, R1은 히드록시 보호기임)을 사산화오스뮴으로 산화시켜 하기 일반식의 광학적 활성 디올 :을 수득하는 단계 ; b) 상기 단계(a)의 디올 생성물에 약산 촉매의 존재하에 일반식 : R4-C-(O-R3)3(이때 R3은 메틸 또는 에틸이고, R4는 탄소수가 1 내지 6개인 직쇄 또는 측쇄 알킬 또는 페닐임)의 트리메틸 또는 트리에틸 오르토에스테르로 처리함으로써 하기 일반식의 시클릭 오르토에스테르 :로 전환시키는 단계 ; c) 상기 단계(b)의 시클릭 오르토에스테르 생성물에 루이스산 촉매로 처리함으로써 하기 일반식의 광학적 활성 시클로부탄온 :을 수득하는 단계 ; b) 상기 단계(c)의 광학적 활성 시클로부탄온 생성물에 환원제를 처리하여 하기 일반식의 광학적 활성 시클로부탄올 :을 수득하는 단계 ; e) 상기 단계(d)의 광학적 활성 시클로부탄올 생성물에 하기 일반식의 광학적 활성 시클로부탄 화합물 :(이때, X는 이탈기임)로 전화시키는 단계 ; f) 상기 단계(e)의 생성물에 하기 식의 푸린 :과 반응시켜 하기 일반식의 광학적 활성 화합물 :(이때, R5는 6-옥소 치환체로 전환될 수 있는 기이다)을 수득하는 단계 ; 및 g) 상기 단계(f)의 생성물에서 R1히드록시 보호기를 제거하고, R5기를 6-옥소로 전환시키는 단계를 포함하는 항바이러스제〔1R-(1α,2β,3α)〕-2-아미노-9-〔2,3-비스(히드록시메틸)시클로부틸〕-1,9-디히드로-6H-푸린-6-온의 제조 방법.
- a) 하기 일반식의 광학적 활성 3-메틸렌 화합물 :(이때, R1은 히드록시 보호기임)을 사산화오스뮴으로 산화시켜 하기 일반식의 광학적 활성 디올 :을 수득하는 단계 ; b) 상기 단계(a)의 디올 생성물에 약산 촉매의 존재하에 일반식 : R4-C-(O-R3)3(이때 R3은 메틸 또는 에틸이고, R4는 탄소수가 1 내지 6개인 직쇄 또는 측쇄 알킬 또는 페닐임)의 트리메틸 또는 트리에틸 오르토에스테르로 처리함으로써 하기 일반식의 시클릭 오르토에스테르 :로 전환시키는 단계 ; c) 상기 단계(b)의 시클릭 오르토에스테르 생성물에 루이스산 촉매로 처리함으로써 하기 일반식의 광학적 활성 시클로부탄온 :을 수득하는 단계 ; b) 상기 단계(c)의 광학적 활성 시클로부탄온 생성물에 환원제를 처리하여 하기 일반식의 광학적 활성 시클로부탄올 :을 수득하는 단계 ; e) 상기 단계(d)의 광학적 활성 시클로부탄올 생성물에 하기 일반식의 광학적 활성 시클로부탄 화합물 :(이때, X는 이탈기임)로 전화시키는 단계 ; f) 상기 단계(e)의 생성물에 하기 식의 푸린염 :(이때, Y1은 요오도, 브로모 또는 클로로이고, R5, R6, R7및 R8은 독립적으로 탄소수가 1 내지 10개인 직쇄 또는 측쇄 알킬, 치환체가 탄소수가 1 내지 6개인 알콕시 또는 아릴인 탄소수 1 내지 10개의 치환된 알키로 구성된 군으로부터 선택함)과 반응시켜 하기 일반식의 광학적 활성 화합물 :을 수득하는 단계 ; 및 g) 상기 단계(f)의 생성물에서 R1히드록시 보호기를 제거하고, Y1기를 6-옥소로 전환시키는 단계를 포함하는 항바이러스제〔1R-(1α,2β,3α)〕-2-아미노-9-〔2,3-비스(히드록시메틸)시클로부틸〕-1,9-디히드로-6H-푸린-6-온의 제조 방법.
- 하기 일반식의 화합물 :(이때, R1은 t-부틸디메틸실릴, t-부틸디페닐실릴, (트리페닐메틸)디메틸실릴, 메틸디이소프로필실릴, 트리이소프로실실릴, 벤질, p-메톡시벤질, 트리페닐메틸, 4-메톡시 치환 트리페닐메틸, 4,4-디메톡시 치환 트리페닐메틸, 또는이고 ; R2는 탄소수가 1 내지 6개인 직쇄 또는 측쇄 알킬 또는 페닐이다.
- 제7항에 있어서, (1S-트랜스)-3-히드록시-1,2,3-시클로프로판트리메탄올, a1, a2,-디벤조에이트인 화합물.
- 하기 일반식의 화합물 :(이때, R1은 t-부틸디메틸실릴, t-부틸디페닐실릴, (트리페닐메틸)디메틸실릴, 메틸디이소프로필실릴, 트리이소프로실실릴, 벤질, p-메톡시벤질, 트리페닐메틸, 4-메톡시 치환 트리페닐메틸, 4,4-디메톡시 치환 트리페닐메틸, 또는이고 ; R2는 탄소수가 1 내지 6개인 직쇄 또는 측쇄 알킬 또는 페닐이다.
- 제9항에 있어서, (1S, 2S)-5-메톡시-5-메틸-4,6-디옥사스피로〔2. 4〕헵탄-1,2-디메탄올, 디벤조에이트인 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| US41640395A | 1995-04-03 | 1995-04-03 | |
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| EP (1) | EP0736533A1 (ko) |
| JP (1) | JPH08283276A (ko) |
| KR (1) | KR960037634A (ko) |
| CN (1) | CN1151982A (ko) |
| AU (1) | AU706900B2 (ko) |
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| US6353122B1 (en) | 1997-02-26 | 2002-03-05 | Bristol-Myers Squibb Company | Method for epoxidation of 3-methylenecyclopropanes |
| AU2004224191A1 (en) | 2003-03-24 | 2004-10-07 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| CN1898569A (zh) | 2003-10-24 | 2007-01-17 | 伊缪因艾德有限公司 | 治疗方法 |
| US20060292073A1 (en) * | 2005-06-23 | 2006-12-28 | Emory University | Stereoselective Synthesis of Amino Acid Analogs for Tumor Imaging |
| WO2007001940A2 (en) * | 2005-06-23 | 2007-01-04 | Emory University | Imaging agents |
| KR20080056220A (ko) | 2005-10-19 | 2008-06-20 | 에프. 호프만-라 로슈 아게 | 페닐-아세트아마이드 ｎｎｒｔ 저해제 |
| PT2057125E (pt) | 2006-08-16 | 2011-05-31 | Hoffmann La Roche | Inibidores n?o nucle?sidos de transcriptase inversa |
| ES2550152T3 (es) | 2006-12-13 | 2015-11-04 | F. Hoffmann-La Roche Ag | Derivados de 2-(piperidin-4-il)-4-fenoxi-o fenilamino-pirimidina como inhibidores no nucleósidos de transcriptasa inversa |
| WO2008145562A1 (en) | 2007-05-30 | 2008-12-04 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| WO2009080534A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| US8246752B2 (en) | 2008-01-25 | 2012-08-21 | Clear Catheter Systems, Inc. | Methods and devices to clear obstructions from medical tubes |
| ES2548508T3 (es) | 2009-05-27 | 2015-10-19 | Biotempus Limited | Métodos de tratamiento de enfermedades |
| WO2011077100A1 (en) | 2009-12-24 | 2011-06-30 | Cipla Limited | Antiretroviral composition |
| CN115181013B (zh) * | 2022-07-22 | 2023-08-08 | 北京先通国际医药科技股份有限公司 | 修饰脂肪酸型pet试剂前体关键中间体的制备方法及其用途 |
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| US4855466A (en) * | 1987-12-28 | 1989-08-08 | E. R. Squibb & Sons, Inc. | Purinyl cyclobutanes |
| US5126345A (en) * | 1988-03-30 | 1992-06-30 | E. R. Squibb & Sons, Inc. | Bis (hydroxymethyl) cyclobutyl triazolopyrimidines |
| US5723609A (en) * | 1988-03-30 | 1998-03-03 | E. R. Squibb & Sons, Inc. | Bis (hydroxymethyl) cyclobutyl purines |
| AU622926B2 (en) * | 1988-09-09 | 1992-04-30 | Nippon Kayaku Kabushiki Kaisha | Pyrimidine or purine cyclobutane derivatives |
| US5153352A (en) * | 1988-10-25 | 1992-10-06 | Bristol-Myers Squibb Company | Process for preparation of intermediates of carbocyclic nucleoside analogs |
| US5064961A (en) * | 1989-12-18 | 1991-11-12 | E. R. Squibb & Sons, Inc. | Process for preparing an optically active cyclobutane nucleoside |
| US5250697A (en) * | 1990-03-01 | 1993-10-05 | Nippon Kayaku Kabushiki Kaisha | Cyclobutane derivatives |
| US5235052A (en) * | 1990-04-16 | 1993-08-10 | Bristol-Myers Squibb Company | Process for preparing substituted cyclobutane purines |
| AU635642B2 (en) * | 1990-05-24 | 1993-03-25 | E.R. Squibb & Sons, Inc. | Fluorinated bis(hydroxymethyl) cyclobutyl purines and pyrimidines |
| US5233076A (en) * | 1990-05-24 | 1993-08-03 | E. R. Squibb & Sons, Inc. | Process for preparing an optically active cyclobutanone, an intermediate in the synthesis of an optically active cyclobutane nucleoside |
| USH1142H (en) * | 1990-11-05 | 1993-02-02 | Optically active cyclobutyl pyrimidine | |
| US5185463A (en) * | 1991-10-02 | 1993-02-09 | E. R. Squibb & Sons, Inc. | Process for the preparation of an antiviral agent |
| JP2974181B2 (ja) * | 1991-10-09 | 1999-11-08 | 日本化薬株式会社 | シクロブタノールの新規な製造法 |
| US5412134A (en) * | 1992-05-26 | 1995-05-02 | E. R. Squibb & Sons, Inc. | Process for preparing diprotected 2,3-hydroxymethyl cyclobutanol |
| US5874578A (en) * | 1992-07-13 | 1999-02-23 | Bristol-Myers Squibb | Process for preparing guanine-containing antiviral agents and purinyl salts useful in such process |
| JPH06107589A (ja) * | 1992-09-25 | 1994-04-19 | Nippon Kayaku Co Ltd | シクロブタノン誘導体の製造法 |
| JP3074432B2 (ja) * | 1994-01-27 | 2000-08-07 | 矢崎総業株式会社 | ロック付きコネクタハウジング |
-
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- 1996-04-01 JP JP8078890A patent/JPH08283276A/ja active Pending
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- 1996-04-02 KR KR1019960009829A patent/KR960037634A/ko not_active Application Discontinuation
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| HUP9600852A2 (en) | 1996-12-30 |
| IL117574A0 (en) | 1996-07-23 |
| JPH08283276A (ja) | 1996-10-29 |
| HU9600852D0 (en) | 1996-05-28 |
| CA2172660A1 (en) | 1996-10-04 |
| EP0736533A1 (en) | 1996-10-09 |
| SG44742A1 (en) | 1997-12-19 |
| AU706900B2 (en) | 1999-07-01 |
| US5773614A (en) | 1998-06-30 |
| CN1151982A (zh) | 1997-06-18 |
| AU5043896A (en) | 1996-10-17 |
| MX9601180A (es) | 1997-02-01 |
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