KR890003439B1 - 뉴클레오시드 및 이의 제조방법 - Google Patents
뉴클레오시드 및 이의 제조방법 Download PDFInfo
- Publication number
- KR890003439B1 KR890003439B1 KR1019850009042A KR850009042A KR890003439B1 KR 890003439 B1 KR890003439 B1 KR 890003439B1 KR 1019850009042 A KR1019850009042 A KR 1019850009042A KR 850009042 A KR850009042 A KR 850009042A KR 890003439 B1 KR890003439 B1 KR 890003439B1
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- KR
- South Korea
- Prior art keywords
- desoxy
- compound
- formula
- amino
- difluororibose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002777 nucleoside Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000003835 nucleoside group Chemical group 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 75
- 206010028980 Neoplasm Diseases 0.000 claims description 46
- -1 4-amino-5-methyl-2-oxo-1H-pyrimidin-1-yl Chemical group 0.000 claims description 44
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 12
- 150000001720 carbohydrates Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000009826 neoplastic cell growth Effects 0.000 claims description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- BDYOVGXZAQDDGF-INEUFUBQSA-N 4-amino-1-[(3r,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]pyrimidin-2-one Chemical compound NC=1C=CN(C(=O)C(F)(F)[C@H](O)[C@H](O)CO)C(=O)N=1 BDYOVGXZAQDDGF-INEUFUBQSA-N 0.000 claims description 5
- BDYOVGXZAQDDGF-XINAWCOVSA-N 4-amino-1-[(3s,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]pyrimidin-2-one Chemical compound NC=1C=CN(C(=O)C(F)(F)[C@@H](O)[C@H](O)CO)C(=O)N=1 BDYOVGXZAQDDGF-XINAWCOVSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- AQKXPKQQTIZCTL-INEUFUBQSA-N 1-[(3r,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]pyrimidine-2,4-dione Chemical compound OC[C@@H](O)[C@@H](O)C(F)(F)C(=O)N1C=CC(=O)NC1=O AQKXPKQQTIZCTL-INEUFUBQSA-N 0.000 claims description 4
- 238000002512 chemotherapy Methods 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 25
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
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- 239000000706 filtrate Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
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- 229920005989 resin Polymers 0.000 description 12
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000014633 carbohydrates Nutrition 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- QDWXEYDAUGYGIF-NQXXGFSBSA-N 2-chloro-9-[(3r,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]-3h-purin-6-one Chemical compound N1=C(Cl)NC(=O)C2=C1N(C(=O)C(F)(F)[C@H](O)[C@H](O)CO)C=N2 QDWXEYDAUGYGIF-NQXXGFSBSA-N 0.000 description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002596 lactones Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
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- 238000010561 standard procedure Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
- JUBHYRUGQZKAMO-INEUFUBQSA-N (3r,4r)-1-(6-aminopurin-9-yl)-2,2-difluoro-3,4,5-trihydroxypentan-1-one Chemical compound NC1=NC=NC2=C1N=CN2C(=O)C(F)(F)[C@H](O)[C@H](O)CO JUBHYRUGQZKAMO-INEUFUBQSA-N 0.000 description 3
- GXIKNHADGMHKMI-AURTYUHDSA-N (3s,4r)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2,2-difluoro-3,4,5-trihydroxypentanoic acid Chemical compound CC(C)(C)[Si](C)(C)OC(O)[C@@H](O)[C@@](O)(C(F)(F)C(O)=O)O[Si](C)(C)C(C)(C)C GXIKNHADGMHKMI-AURTYUHDSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JBSWWQRUJIDCJA-NQXXGFSBSA-N 2-amino-9-[(3r,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]-3h-purin-6-one Chemical compound O=C1NC(N)=NC2=C1N=CN2C(=O)C(F)(F)[C@H](O)[C@H](O)CO JBSWWQRUJIDCJA-NQXXGFSBSA-N 0.000 description 3
- XOHVRRONTCFJKX-PHDIDXHHSA-N 4-amino-1-[(3r,4r)-2,2-difluoro-3,4,5-trihydroxypentanoyl]-5-methylpyrimidin-2-one Chemical compound CC1=CN(C(=O)C(F)(F)[C@H](O)[C@H](O)CO)C(=O)N=C1N XOHVRRONTCFJKX-PHDIDXHHSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
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- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
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- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
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- XMASOCWIKFSBEC-YTSPXQHTSA-N methylsulfonyl (3s,4r)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2,2-difluoro-3,4,5-trihydroxypentanoate Chemical compound CC(C)(C)[Si](C)(C)OC(O)[C@@H](O)[C@](O)(O[Si](C)(C)C(C)(C)C)C(F)(F)C(=O)OS(C)(=O)=O XMASOCWIKFSBEC-YTSPXQHTSA-N 0.000 description 3
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 125000002221 trityl group Chemical group [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 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67778384A | 1984-12-04 | 1984-12-04 | |
| US677,7830 | 1984-12-04 | ||
| US78641985A | 1985-10-10 | 1985-10-10 | |
| US786,419 | 1985-10-10 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890006677A Division KR890003426B1 (ko) | 1984-12-04 | 1989-05-18 | 뉴클레오시드 및 이의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR860004920A KR860004920A (ko) | 1986-07-16 |
| KR890003439B1 true KR890003439B1 (ko) | 1989-09-21 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850009042A Expired KR890003439B1 (ko) | 1984-12-04 | 1985-12-03 | 뉴클레오시드 및 이의 제조방법 |
| KR1019890006677A Expired KR890003426B1 (ko) | 1984-12-04 | 1989-05-18 | 뉴클레오시드 및 이의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890006677A Expired KR890003426B1 (ko) | 1984-12-04 | 1989-05-18 | 뉴클레오시드 및 이의 제조방법 |
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|---|---|
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| JP (1) | JPH0637394B2 (cg-RX-API-DMAC10.html) |
| KR (2) | KR890003439B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN1020194C (cg-RX-API-DMAC10.html) |
| AT (1) | ATE92499T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU581269B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1264738A (cg-RX-API-DMAC10.html) |
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| DE (1) | DE3587500T2 (cg-RX-API-DMAC10.html) |
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| ES (1) | ES8801546A1 (cg-RX-API-DMAC10.html) |
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| HK (1) | HK113693A (cg-RX-API-DMAC10.html) |
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Families Citing this family (160)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1269659A (en) * | 1984-08-06 | 1990-05-29 | Brigham Young University | Method for the production of 2'-deoxyadenosine compounds |
| CA1295998C (en) * | 1985-07-29 | 1992-02-18 | Sai P. Sunkara | Nucleosides and their use as antineoplastic agents |
| US4814438A (en) * | 1986-12-24 | 1989-03-21 | Eli Lilly And Company | Immunoglobulin conjugates of 2',2'-difluronucleosides |
| US4994558A (en) * | 1986-12-24 | 1991-02-19 | Eli Lilly And Company | Immunoglobulin conjugates |
| IL84842A0 (en) * | 1986-12-24 | 1988-06-30 | Lilly Co Eli | Immunoglobulin conjugates |
| DE3856158T2 (de) * | 1987-08-28 | 1998-08-20 | Lilly Co Eli | Verfahren zur Herstellung von Zwischenverbindungen verwendbar in der Herstellung von 2',2'-Difluoronucleosiden |
| US4965374A (en) * | 1987-08-28 | 1990-10-23 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| US5223608A (en) * | 1987-08-28 | 1993-06-29 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| US4914028A (en) * | 1988-02-10 | 1990-04-03 | Eli Lilly And Company | Method of preparing beta-2',2'-difluoronucleosides |
| CA1312599C (en) * | 1988-02-16 | 1993-01-12 | Larry Wayne Hertel | 2',3'dideoxy-2',2'difluoronucleosides |
| US5644043A (en) * | 1988-02-16 | 1997-07-01 | Eli Lilly And Company | 2',3'-dideoxy-2',2'-difluoronucleosides and intermediates |
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| US12703750B2 (en) | 2020-04-11 | 2026-08-11 | Northwestern University | Humanized antibody targeting the tumor associated antigen IL13Ra2 |
| GB202019692D0 (en) | 2020-12-14 | 2021-01-27 | Apterna Ltd | Aptamer-sirna fusions |
| WO2023091887A1 (en) | 2021-11-16 | 2023-05-25 | Genentech, Inc. | Methods and compositions for treating systemic lupus erythematosus (sle) with mosunetuzumab |
| WO2026082894A1 (en) | 2024-10-17 | 2026-04-23 | Sanofi | Ceacam5 antibody-drug conjugate for use in cancer therapy |
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| DE147774C (cg-RX-API-DMAC10.html) * | ||||
| US3705147A (en) * | 1969-08-22 | 1972-12-05 | Univ Utah | 3-deazapyrimidine nucleosides and method of preparation thereof |
| US3870700A (en) * | 1973-05-29 | 1975-03-11 | Miles Lab | 2-halogeno-2-deoxy-5-(substituted)uridines |
| JPS5136467A (en) * | 1974-09-20 | 1976-03-27 | Tanabe Seiyaku Co | 11 beetaa dd2** harogeno 2** deokishiribofuranoshirurashirujudotai no seiho |
| DE2628202A1 (de) * | 1976-06-23 | 1977-12-29 | Max Planck Gesellschaft | Verfahren zur herstellung von 2'-substituierten-d-ribofuranosylpurinderivaten |
| US4058602A (en) * | 1976-08-09 | 1977-11-15 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Synthesis, structure, and antitumor activity of 5,6-dihydro-5-azacytidine |
| US4211773A (en) * | 1978-10-02 | 1980-07-08 | Sloan Kettering Institute For Cancer Research | 5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides |
| US4526988A (en) * | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| ZA859008B (en) * | 1984-12-04 | 1987-07-29 | Lilly Co Eli | The treatment of tumors in mammals |
| CA1295998C (en) * | 1985-07-29 | 1992-02-18 | Sai P. Sunkara | Nucleosides and their use as antineoplastic agents |
| US4914028A (en) * | 1988-02-10 | 1990-04-03 | Eli Lilly And Company | Method of preparing beta-2',2'-difluoronucleosides |
| US4983724A (en) * | 1988-02-16 | 1991-01-08 | Eli Lilly And Company | Inversion of 2,2-difluororibose to a 2,2-difluoroxylose and intermediates therefor |
| JPH0232093A (ja) * | 1988-06-08 | 1990-02-01 | Merrell Dow Pharmaceut Inc | 抗レトロウィルスジフルオロ化ヌクレオシド類 |
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1985
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- 1985-11-25 IL IL77133A patent/IL77133A/xx not_active IP Right Cessation
- 1985-11-25 AT AT85308547T patent/ATE92499T1/de not_active IP Right Cessation
- 1985-11-25 CA CA000496077A patent/CA1264738A/en not_active Expired - Lifetime
- 1985-11-25 EP EP85308547A patent/EP0184365B1/en not_active Expired - Lifetime
- 1985-11-26 PT PT81559A patent/PT81559B/pt unknown
- 1985-11-27 GR GR852858A patent/GR852858B/el unknown
- 1985-11-28 DK DK549685A patent/DK162965C/da not_active IP Right Cessation
- 1985-11-28 NZ NZ214364A patent/NZ214364A/xx unknown
- 1985-11-28 PH PH33109A patent/PH23172A/en unknown
- 1985-12-02 AU AU50555/85A patent/AU581269B2/en not_active Expired
- 1985-12-03 HU HU854620A patent/HU194273B/hu unknown
- 1985-12-03 EG EG771/85A patent/EG17765A/xx active
- 1985-12-03 IE IE303885A patent/IE60328B1/en not_active IP Right Cessation
- 1985-12-03 CN CN85109409A patent/CN1020194C/zh not_active Expired - Lifetime
- 1985-12-03 JP JP60273161A patent/JPH0637394B2/ja not_active Expired - Lifetime
- 1985-12-03 ES ES549547A patent/ES8801546A1/es not_active Expired
- 1985-12-03 KR KR1019850009042A patent/KR890003439B1/ko not_active Expired
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1989
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1993
- 1993-10-21 HK HK1136/93A patent/HK113693A/en not_active IP Right Cessation
-
1994
- 1994-07-26 US US08/280,687 patent/US5464826A/en not_active Expired - Lifetime
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1995
- 1995-09-08 CY CY180695A patent/CY1806A/xx unknown
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|---|---|
| DK162965B (da) | 1992-01-06 |
| CN85109409A (zh) | 1986-08-27 |
| DK549685A (da) | 1986-06-05 |
| DE3587500D1 (de) | 1993-09-09 |
| JPS61148193A (ja) | 1986-07-05 |
| NZ214364A (en) | 1988-11-29 |
| PT81559A (en) | 1985-12-01 |
| ES8801546A1 (es) | 1987-08-01 |
| KR860004920A (ko) | 1986-07-16 |
| PT81559B (pt) | 1988-03-03 |
| CA1264738A (en) | 1990-01-23 |
| EP0184365A3 (en) | 1988-01-27 |
| IE853038L (en) | 1986-06-04 |
| HUT39188A (en) | 1986-08-28 |
| HK113693A (en) | 1993-10-29 |
| IL77133A (en) | 1991-01-31 |
| GR852858B (cg-RX-API-DMAC10.html) | 1986-03-28 |
| DK162965C (da) | 1992-06-01 |
| EP0184365B1 (en) | 1993-08-04 |
| CN1020194C (zh) | 1993-03-31 |
| PH23172A (en) | 1989-05-19 |
| KR890003426B1 (ko) | 1989-09-20 |
| IE60328B1 (en) | 1994-06-29 |
| JPH0637394B2 (ja) | 1994-05-18 |
| DK549685D0 (da) | 1985-11-28 |
| EP0184365A2 (en) | 1986-06-11 |
| US5464826A (en) | 1995-11-07 |
| ES549547A0 (es) | 1987-08-01 |
| HU194273B (en) | 1988-01-28 |
| AU581269B2 (en) | 1989-02-16 |
| AU5055585A (en) | 1986-06-12 |
| CY1806A (en) | 1995-09-08 |
| DE3587500T2 (de) | 1993-12-16 |
| ATE92499T1 (de) | 1993-08-15 |
| EG17765A (en) | 1990-08-30 |
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