DD239595A5 - Verfahren zur herstellung neuer nucleosidderivate - Google Patents

Verfahren zur herstellung neuer nucleosidderivate Download PDF

Info

Publication number: DD239595A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; formula; group; general formula; bromovinyl
Prior art date: 1984-10-12

Application number

DD85281660A

Other languages

German (de)

English (en)

Inventor

Anna Szabolcs

Laszlo Oetvoes

Attila Szemzoe

Helga Tuedoes

Janos Sagi

Original Assignee

��@��@��@��@��k��

Priority date (The priority date 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 date listed.)

1984-10-12

Filing date

1985-10-11

Publication date

1986-10-01

1985-10-11 Application filed by ��@��@��@��@��k�� filed Critical ��@��@��@��@��k��

1986-10-01 Publication of DD239595A5 publication Critical patent/DD239595A5/de

Links

150000003833 nucleoside derivatives Chemical class 0.000 title abstract description 9
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 72
125000002252 acyl group Chemical group 0.000 claims abstract description 28
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
230000000903 blocking effect Effects 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 5
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 4
125000003435 aroyl group Chemical group 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
230000000840 anti-viral effect Effects 0.000 abstract description 13
239000003814 drug Substances 0.000 abstract description 5
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 4
231100000419 toxicity Toxicity 0.000 abstract description 4
230000001988 toxicity Effects 0.000 abstract description 4
-1 5-substituted uracil Chemical class 0.000 description 58
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DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 12
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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RHQQHZQUAMFINJ-GKWSUJDHSA-N 1-[(3s,5s,8s,9s,10s,11s,13s,14s,17s)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@H]21 RHQQHZQUAMFINJ-GKWSUJDHSA-N 0.000 description 2
BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
GCQYYIHYQMVWLT-YPLKXGEDSA-N 5-[(e)-2-bromoethenyl]-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 GCQYYIHYQMVWLT-YPLKXGEDSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000700584 Simplexvirus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
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238000000338 in vitro Methods 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000008297 liquid dosage form Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002609 medium Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
125000003835 nucleoside group Chemical group 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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239000013558 reference substance Substances 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
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230000003862 health status Effects 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000001524 infective effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Chemical class 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
JCAJLOTWCAOOEJ-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1.CC1CCCCC1.CC1CCCCC1 JCAJLOTWCAOOEJ-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000008107 starch Chemical class 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

DD85281660A 1984-10-12 1985-10-11 Verfahren zur herstellung neuer nucleosidderivate DD239595A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU843821A HU192472B (en)	1984-10-12	1984-10-12	Process for preparing /e/-5-/2-bromo-vinyl/-uracyl derivatives

Publications (1)

Publication Number	Publication Date
DD239595A5 true DD239595A5 (de)	1986-10-01

Family

ID=10965655

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85281660A DD239595A5 (de)	1984-10-12	1985-10-11	Verfahren zur herstellung neuer nucleosidderivate

Country Status (18)

Country	Link
JP (1)	JPS61126097A (da)
KR (1)	KR870001935B1 (da)
AT (1)	ATA294685A (da)
BE (1)	BE903381A (da)
DD (1)	DD239595A5 (da)
DE (1)	DE3536604A1 (da)
DK (1)	DK465585A (da)
ES (1)	ES8605819A1 (da)
FI (1)	FI853969A7 (da)
FR (1)	FR2571726A1 (da)
GB (1)	GB2165539A (da)
HU (1)	HU192472B (da)
IL (1)	IL76661A0 (da)
IT (1)	IT1186775B (da)
NL (1)	NL8502794A (da)
NO (1)	NO854041L (da)
PL (1)	PL255741A1 (da)
SE (1)	SE8504708L (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8912972D0 (en) *	1989-06-06	1989-07-26	Wellcome Found	Therapeutic nucleosides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5136498A (ja) *	1974-09-20	1976-03-27	Tanabe Seiyaku Co	22*anhidoroarabinofuranoshirurashirujudotainoseiho
JPS5687599A (en) *	1979-12-19	1981-07-16	Yamasa Shoyu Co Ltd	E 55 22halogenovinyl arabinofuranosyluracil and its preparation
NZ199764A (en) *	1981-03-20	1984-08-24	Beecham Group Plc	5-(2-halogenovinyl)-2'-deoxyuridine derivatives and pharmaceutical compositions

1984
- 1984-10-12 HU HU843821A patent/HU192472B/hu not_active IP Right Cessation
1985
- 1985-10-07 BE BE1/011346A patent/BE903381A/fr not_active IP Right Cessation
- 1985-10-10 FR FR8515026A patent/FR2571726A1/fr not_active Withdrawn
- 1985-10-11 ES ES547820A patent/ES8605819A1/es not_active Expired
- 1985-10-11 KR KR1019850007493A patent/KR870001935B1/ko not_active Expired
- 1985-10-11 DK DK465585A patent/DK465585A/da not_active Application Discontinuation
- 1985-10-11 DD DD85281660A patent/DD239595A5/de unknown
- 1985-10-11 PL PL25574185A patent/PL255741A1/xx unknown
- 1985-10-11 FI FI853969A patent/FI853969A7/fi not_active Application Discontinuation
- 1985-10-11 GB GB08525152A patent/GB2165539A/en not_active Withdrawn
- 1985-10-11 JP JP60226674A patent/JPS61126097A/ja active Pending
- 1985-10-11 NL NL8502794A patent/NL8502794A/nl not_active Application Discontinuation
- 1985-10-11 AT AT852946A patent/ATA294685A/de not_active Application Discontinuation
- 1985-10-11 NO NO854041A patent/NO854041L/no unknown
- 1985-10-11 IT IT22442/85A patent/IT1186775B/it active
- 1985-10-11 IL IL76661A patent/IL76661A0/xx unknown
- 1985-10-11 SE SE8504708A patent/SE8504708L/xx not_active Application Discontinuation
- 1985-10-14 DE DE19853536604 patent/DE3536604A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
FI853969L (fi)	1986-04-13
DK465585A (da)	1986-04-13
HU192472B (en)	1987-06-29
FI853969A0 (fi)	1985-10-11
ATA294685A (de)	1987-03-15
PL255741A1 (en)	1986-08-12
NO854041L (no)	1986-04-14
DK465585D0 (da)	1985-10-11
ES547820A0 (es)	1986-04-01
IT1186775B (it)	1987-12-16
BE903381A (fr)	1986-04-07
KR860003270A (ko)	1986-05-21
SE8504708D0 (sv)	1985-10-11
NL8502794A (nl)	1986-05-01
JPS61126097A (ja)	1986-06-13
IL76661A0 (en)	1986-02-28
IT8522442A0 (it)	1985-10-11
DE3536604A1 (de)	1986-04-17
FI853969A7 (fi)	1986-04-13
FR2571726A1 (fr)	1986-04-18
HUT38655A (en)	1986-06-30
SE8504708L (sv)	1986-04-13
GB2165539A (en)	1986-04-16
KR870001935B1 (ko)	1987-10-22
GB8525152D0 (en)	1985-11-13
ES8605819A1 (es)	1986-04-01

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DE69012840T2 (de)	1995-03-16	Adenosin-Derivate, die eine Aktivität gegen Bluthochdruck haben.
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EP0056265B1 (de)	1985-05-15	5'-Ester von Pyrimidinnucleosiden mit antiviraler Wirksamkeit, Verfahren zur Herstellung und daraus hergestellte Arzneimittel
DD282229A5 (de)	1990-09-05	Verfahren zur herstellung von therapeutischen acyclischen nucleosiden
DD216468A5 (de)	1984-12-12	Verfahren zur herstellung von nucleosiden
DE3739366A1 (de)	1988-10-27	Desaza-purin-nucleosid-derivate, verfahren zu deren herstellung sowie deren verwendung bei der nucleinsaeure-sequenzierung sowie als antivirale mittel
DE2858802C2 (de)	1991-10-02	Arzneimittel zur unterdrueckung von tumorzellwachstum
EP0311100A2 (de)	1989-04-12	Neue Dideoxycytidin-Derivate, ihre Herstellung und Verwendung für Pharmazeutika
EP0355031A2 (de)	1990-02-21	Substituierte Pyrimidinnucleoside, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
DE60012288T2 (de)	2005-08-18	Antivirale pyrimidindion-derivate und verfahren zu ihrer herstellung
DE68923913T2 (de)	1996-01-11	Neplanocinderivate.
CH503037A (de)	1971-02-15	Verfahren zur Herstellung von Pyrimidin-nucleosiden und -nucleotiden
DE69128626T2 (de)	1998-05-20	Enzyminaktivatoren
DE2512609A1 (de)	1976-08-26	Pharmazeutische zubereitung
EP0314011A2 (de)	1989-05-03	Purinderivate
CH642668A5 (de)	1984-04-30	2,6-diaminonebularine, verfahren zu deren herstellung und sie enthaltende pharmazeutische praeparate.
DD239595A5 (de)	1986-10-01	Verfahren zur herstellung neuer nucleosidderivate
DE2921844C2 (de)	1984-11-22	1-(2-Chlorethyl)-1-nitroso-3-substituierte-3-glycosylharnstoffe, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Zubereitungen
DE2410201C3 (de)	1978-08-10	6-Substituierte 3-Carbäthoxyhydrazinopyridazine beziehungsweise ihre Salze sowie solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben
DE2917890C2 (da)	1987-10-29
DE2511829C2 (da)	1989-06-22