KR840001169A - 항비루스성 화합물의 제조방법 - Google Patents
항비루스성 화합물의 제조방법 Download PDFInfo
- Publication number
- KR840001169A KR840001169A KR1019820003589A KR820003589A KR840001169A KR 840001169 A KR840001169 A KR 840001169A KR 1019820003589 A KR1019820003589 A KR 1019820003589A KR 820003589 A KR820003589 A KR 820003589A KR 840001169 A KR840001169 A KR 840001169A
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- KR
- South Korea
- Prior art keywords
- group
- compound
- formula
- atom
- salt
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 13
- 238000000034 method Methods 0.000 title claims 13
- 230000000840 anti-viral effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 11
- 150000002148 esters Chemical class 0.000 claims 7
- 125000003277 amino group Chemical group 0.000 claims 6
- 229910052721 tungsten Inorganic materials 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 238000004517 catalytic hydrocracking Methods 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- (a) 다음 구조식(Ⅱ) 화합물을 탈폐쇄시켜 구조식(Ⅰ)화합물 또는 염 또는 이들의 에스테르를 얻으며 :(b) 다음 구조식(Ⅲ)화합물 또는 염 또는 이들의 에스테르를 구조식(Ⅰ)화합물 또는 염 또는 이들의 에스테르 전환시키며 :(c) 구조식(Ⅳ)의 화합물 또는 염 또는 이들의 에스테르를 기지 방법으로 환원하고 :(d) 다음 구조식(Ⅴ)화합물을 다음 구조식(Ⅵ)화합물과 반응시키고 :(e) 다음 구조식(Ⅶ)의 화합물을 가수분해하고 임의로 다음과 같이 전환시키며 :i) 결과 생성물이 염기일때, 언급한 염기를 생리학적으로 허용될 수 있는 이들의 산부가염으로 전환 :ii) 결과 생성물이 산부가염일때, 언급한 염을 모염기로 전환 :iii) 결과 생성물이 구조식(Ⅰ)의 화합물 또는 이들의 염일때, 언급한화합물 또는 이들의 염을 언급한 화합물 또는 염의 생리학적으로 허용될 수 있는 에스테르로 전환시키거나 또는iv) 결과 생성물이 구조식(Ⅰ)화합물의 에스테르일때, 언급한 에스테르를 구조식(Ⅰ)의 모화합물 또는 생리학적으로 허용될 수 있는 이들의 염으로 전환시키는 것을 특징으로 하는 일반 구조식(Ⅰ)화합물 또는 생리학적으로 허용할 수 있는 염류와 이들의 에스테르를 제조하는 방법.상기 구조식에서, R은 하이드록시 또는 아미노그룹이고, X는 산소 또는 황원자, W와 W'은 수소원자 또는 폐쇄 그룹, Y는 수소원자 또는 폐쇄그룹이고, Z는 -OY 또는 -NHY(여기서 Y는 W,W'과 Y의 적어도 하나가 폐쇄 그룹을 나타내는 것을 제공하는 상기 정의한 것이다). M은 6-하이드록시 또는 아미노그룹이고, G는 아미노그룹으로 전환에 의해 대치할 수 있는 그룹 또는 2-아미노그룹이고, M은 원자 또는 아미노 또는 하이드록시 그룹으로 전환에 의해 대치할 수 있는 그룹, Q는 이탈그룹 또는 원자. A는 이탈그룹 또는 원자이다.
- 제1항에 있어서, 폐쇄그룹 W,W'과 Y가 C1-4알카노일, 아로일, 아리메틸과 트리-C1-4알킬실일 폐쇄그룹으로부터 선택되는 공정.
- 제2항에 있어서, 탈폐쇄가 가수분해 또는 수소분해에 의해 수해되는 공정.
- 제1항에 있어서, M 또는 G가 촉매성수소첨가에 의해 아미노그룹으로 전환되는 아지도그룹인공정.
- 제1항에 있어서, M 또는 G가 아미노분해에 의해 아미노그룹으로 전환되는 수소원자 또는 알킬티오 또는 알킬설포닐그룹인 공정.
- 제1항에 있어서, A가 할로겐원자 또는 아실옥시그룹인 공정.
- 제1항에 있어서, Q가 수소원자 또는 아실 또는 트리 -C1-4알킬실일그룹인공정.
- 제1항, 6과 7항에서 반응이 염기존재하에 수행되는 공정.
- 제1항에 있어서, 가수분해가 염기조건하에 수행되는 공정.
- 제1항에 있어서, X가 산소원자이고 R가 하이드록시 그룹인 공정.
- 제1항에 있어서, X가 산소원자이고 R가 아미노 그룹인 공정.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8124444 | 1981-08-11 | ||
GB8124444 | 1981-08-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840001169A true KR840001169A (ko) | 1984-03-28 |
KR880002276B1 KR880002276B1 (ko) | 1988-10-21 |
Family
ID=10523843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8203589A KR880002276B1 (ko) | 1981-08-11 | 1982-08-10 | 항비루스성 화합물의 제조방법 |
Country Status (25)
Country | Link |
---|---|
EP (1) | EP0072027B1 (ko) |
JP (1) | JPS5841879A (ko) |
KR (1) | KR880002276B1 (ko) |
AT (2) | AT380252B (ko) |
AU (1) | AU569462B2 (ko) |
CA (1) | CA1305138C (ko) |
CS (1) | CS594082A2 (ko) |
DD (1) | DD202717A5 (ko) |
DE (1) | DE3278501D1 (ko) |
DK (1) | DK154561C (ko) |
ES (3) | ES514877A0 (ko) |
FI (1) | FI76086C (ko) |
GB (1) | GB2104070B (ko) |
GR (1) | GR76891B (ko) |
HU (1) | HU189609B (ko) |
IE (1) | IE54148B1 (ko) |
MC (1) | MC1475A1 (ko) |
NO (1) | NO158539C (ko) |
NZ (1) | NZ201547A (ko) |
PH (3) | PH19940A (ko) |
PL (3) | PL141281B1 (ko) |
PT (1) | PT75406B (ko) |
ZA (1) | ZA825792B (ko) |
ZM (1) | ZM6082A1 (ko) |
ZW (1) | ZW16882A1 (ko) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5157120A (en) * | 1980-09-16 | 1992-10-20 | Syntex (U.S.A.) Inc. | Guanine derivatives |
US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
NZ201662A (en) * | 1981-08-26 | 1986-07-11 | Merck & Co Inc | 9-(1,3-(and 2,3)-dihydroxy-1-(and 2)-propoxy-methyl)guanine derivatives and methods for their preparation |
IE830186L (en) * | 1982-02-01 | 1983-08-01 | Syntex Inc | Purines |
US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
EP0095813A3 (en) * | 1982-06-01 | 1985-05-08 | THE PROCTER & GAMBLE COMPANY | Penetrating topical pharmaceutical compositions containing 9-(2-hydroxyethoxymethyl) guanine |
US4556659A (en) * | 1982-08-09 | 1985-12-03 | Syntex (U.S.A.) Inc. | Substituted 9-(1-0- or 3-0-monosubstituted or 1,3-Di-0-substituted propoxymethyl)-purines as antiviral agents |
US4462986A (en) * | 1982-11-04 | 1984-07-31 | Ens Bio Logicals, Inc. | Synergistic anti-herpes compositions |
HUT36464A (en) * | 1983-05-24 | 1985-09-30 | Newport Pharmaceuticals | Process for producing erythro-4-amino-3-/2-hydroxy-3-alkyl/-imidazol-5-carboxamide |
AU577303B2 (en) * | 1983-08-18 | 1988-09-22 | Novartis International Pharmaceutical Ltd | 9-substituted-2-amino purines |
US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
EP0141927B1 (en) * | 1983-08-18 | 1991-10-30 | Beecham Group Plc | Antiviral guanine derivatives |
US4897479A (en) * | 1983-09-30 | 1990-01-30 | Merck & Co., Inc. | Arylsulfonyloxy purine intermediates |
EP0138683A3 (en) * | 1983-09-30 | 1988-01-20 | Merck & Co. Inc. | Purine derivatives, their application in anti-viral compositions |
IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
EP0152316B1 (en) * | 1984-01-26 | 1989-07-26 | Merck & Co. Inc. | Substituted butyl guanines and their utilization in antiviral compositions |
US4621140A (en) * | 1984-02-23 | 1986-11-04 | Syntex (U.S.A.) Inc. | Process for preparing 2,6-substituted-9-(1,3-dihydroxy-2-propoxymethyl)-purines and certain derivatives |
US4579849A (en) * | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
EP0190123A1 (en) * | 1984-07-20 | 1986-08-13 | GAUNTT, Charles, O. | Immunoregulatory and anti-viral compound |
IL78643A0 (en) * | 1985-05-02 | 1986-08-31 | Wellcome Found | Purine derivatives,their preparation and pharmaceutical compositions containing them |
EP0203736B1 (en) | 1985-05-02 | 1989-11-23 | The Wellcome Foundation Limited | Antiviral compounds |
DE3627024A1 (de) | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
US5043339A (en) * | 1988-12-19 | 1991-08-27 | Burroughs Wellcome Co. | Antiviral compounds |
GB8829571D0 (en) * | 1988-12-19 | 1989-02-08 | Wellcome Found | Antiviral compounds |
US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
DE4020481A1 (de) * | 1990-06-27 | 1992-01-02 | Hoechst Ag | Verfahren zur herstellung von substituierten acyclischen nukleosiden und dabei auftretende zwischenprodukte |
US5068119A (en) * | 1990-09-28 | 1991-11-26 | Nabisco Brands, Inc. | Acid-hydrolyzable ester derivatives as low calorie fat mimetics |
US5567816A (en) * | 1994-07-26 | 1996-10-22 | Syntex (U.S.A.) Inc. | Preparation of acyclovir using 1,3 dioxolane |
CA2152863A1 (en) * | 1994-07-26 | 1996-01-27 | Yeun-Kwei Han | Preparation of acyclovir |
US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
US5856481A (en) * | 1994-07-28 | 1999-01-05 | Syntex (U.S.A.) Inc. | 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
US5565565A (en) * | 1994-08-04 | 1996-10-15 | Syntex (U.S.A.) Inc. | Preparation of N-9 substituted guanine compounds |
US5559114A (en) * | 1994-12-16 | 1996-09-24 | Exley; Ray W. | Treatment of autoimmune disease using 2-amino purine derivatives |
US5700936A (en) * | 1996-01-26 | 1997-12-23 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol valinate |
US5840890A (en) * | 1996-01-26 | 1998-11-24 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
US6040446A (en) | 1996-01-26 | 2000-03-21 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol derivative |
US5756736A (en) * | 1996-01-26 | 1998-05-26 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
NZ201662A (en) * | 1981-08-26 | 1986-07-11 | Merck & Co Inc | 9-(1,3-(and 2,3)-dihydroxy-1-(and 2)-propoxy-methyl)guanine derivatives and methods for their preparation |
US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
-
1982
- 1982-08-10 AU AU87020/82A patent/AU569462B2/en not_active Ceased
- 1982-08-10 PT PT75406A patent/PT75406B/pt not_active IP Right Cessation
- 1982-08-10 FI FI822783A patent/FI76086C/fi not_active IP Right Cessation
- 1982-08-10 PL PL1982247393A patent/PL141281B1/pl unknown
- 1982-08-10 MC MC821601A patent/MC1475A1/xx unknown
- 1982-08-10 HU HU822577A patent/HU189609B/hu not_active IP Right Cessation
- 1982-08-10 NO NO822725A patent/NO158539C/no unknown
- 1982-08-10 DK DK359082A patent/DK154561C/da not_active IP Right Cessation
- 1982-08-10 DD DD82242394A patent/DD202717A5/de unknown
- 1982-08-10 ES ES514877A patent/ES514877A0/es active Granted
- 1982-08-10 NZ NZ201547A patent/NZ201547A/en unknown
- 1982-08-10 AT AT0306082A patent/AT380252B/de not_active IP Right Cessation
- 1982-08-10 ZW ZW168/82A patent/ZW16882A1/xx unknown
- 1982-08-10 CS CS825940A patent/CS594082A2/cs unknown
- 1982-08-10 PL PL1982237847A patent/PL141198B1/pl unknown
- 1982-08-10 JP JP57139086A patent/JPS5841879A/ja active Granted
- 1982-08-10 IE IE1921/82A patent/IE54148B1/en not_active IP Right Cessation
- 1982-08-10 EP EP82107247A patent/EP0072027B1/en not_active Expired
- 1982-08-10 AT AT82107247T patent/ATE34393T1/de active
- 1982-08-10 PH PH27698A patent/PH19940A/en unknown
- 1982-08-10 DE DE8282107247T patent/DE3278501D1/de not_active Expired
- 1982-08-10 ZA ZA825792A patent/ZA825792B/xx unknown
- 1982-08-10 GB GB08222977A patent/GB2104070B/en not_active Expired
- 1982-08-10 KR KR8203589A patent/KR880002276B1/ko active
- 1982-08-10 PL PL24739482A patent/PL247394A1/xx unknown
- 1982-08-10 ZM ZM60/82A patent/ZM6082A1/xx unknown
- 1982-08-10 CA CA000409132A patent/CA1305138C/en not_active Expired - Fee Related
- 1982-08-10 GR GR69006A patent/GR76891B/el unknown
-
1983
- 1983-04-15 ES ES521550A patent/ES8504802A1/es not_active Expired
- 1983-04-15 ES ES521551A patent/ES8502117A1/es not_active Expired
- 1983-12-16 PH PH29988A patent/PH18814A/en unknown
- 1983-12-16 PH PH29987A patent/PH20148A/en unknown
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