NL8502794A - Nieuwe nucleoside derivaten met antiherpetische eigenschappen, farmaceutische preparaten met dergelijke derivaten erin en werkwijze voor de bereiding van de werkzame bestanddelen. - Google Patents

Nieuwe nucleoside derivaten met antiherpetische eigenschappen, farmaceutische preparaten met dergelijke derivaten erin en werkwijze voor de bereiding van de werkzame bestanddelen. Download PDF

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Publication number: NL8502794A
Authority: NL; Netherlands
Prior art keywords: formula; compound; optionally substituted; formula sheet; sheet
Prior art date: 1984-10-12

Application number

NL8502794A

Other languages

English (en)

Dutch (nl)

Original Assignee

Mta Koezponti Kemiai Kutato In

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

1986-05-01

1985-10-11 Application filed by Mta Koezponti Kemiai Kutato In filed Critical Mta Koezponti Kemiai Kutato In

1986-05-01 Publication of NL8502794A publication Critical patent/NL8502794A/nl

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238000000034 method Methods 0.000 title claims description 17
150000003833 nucleoside derivatives Chemical class 0.000 title description 7
239000000825 pharmaceutical preparation Substances 0.000 title description 4
239000013543 active substance Substances 0.000 title description 2
230000003602 anti-herpes Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 86
-1 2-bromovinyl Chemical group 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 20
125000002252 acyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
230000000840 anti-viral effect Effects 0.000 claims description 8
230000000903 blocking effect Effects 0.000 claims description 8
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125000001589 carboacyl group Chemical group 0.000 claims description 6
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238000006243 chemical reaction Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
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239000002274 desiccant Substances 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
238000011978 dissolution method Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
206010014599 encephalitis Diseases 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012634 fragment Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229940093915 gynecological organic acid Drugs 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
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
230000001524 infective effect Effects 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 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
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
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 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
238000011160 research Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation 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
230000003612 virological effect Effects 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 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)

NL8502794A 1984-10-12 1985-10-11 Nieuwe nucleoside derivaten met antiherpetische eigenschappen, farmaceutische preparaten met dergelijke derivaten erin en werkwijze voor de bereiding van de werkzame bestanddelen. NL8502794A (nl)

Applications Claiming Priority (2)

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
HU382184		1984-10-12

Publications (1)

Publication Number	Publication Date
NL8502794A true NL8502794A (nl)	1986-05-01

Family

ID=10965655

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8502794A NL8502794A (nl)	1984-10-12	1985-10-11	Nieuwe nucleoside derivaten met antiherpetische eigenschappen, farmaceutische preparaten met dergelijke derivaten erin en werkwijze voor de bereiding van de werkzame bestanddelen.

Country Status (18)

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

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 PL PL25574185A patent/PL255741A1/xx unknown
- 1985-10-11 FI FI853969A patent/FI853969A7/fi not_active Application Discontinuation
- 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 NL NL8502794A patent/NL8502794A/nl not_active Application Discontinuation
- 1985-10-11 DD DD85281660A patent/DD239595A5/de unknown
- 1985-10-11 SE SE8504708A patent/SE8504708L/xx not_active Application Discontinuation
- 1985-10-11 JP JP60226674A patent/JPS61126097A/ja active Pending
- 1985-10-11 NO NO854041A patent/NO854041L/no unknown
- 1985-10-11 IT IT22442/85A patent/IT1186775B/it active
- 1985-10-11 AT AT852946A patent/ATA294685A/de not_active Application Discontinuation
- 1985-10-11 IL IL76661A patent/IL76661A0/xx unknown
- 1985-10-11 GB GB08525152A patent/GB2165539A/en not_active Withdrawn
- 1985-10-14 DE DE19853536604 patent/DE3536604A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
ES8605819A1 (es)	1986-04-01
HUT38655A (en)	1986-06-30
GB8525152D0 (en)	1985-11-13
ES547820A0 (es)	1986-04-01
NO854041L (no)	1986-04-14
ATA294685A (de)	1987-03-15
SE8504708L (sv)	1986-04-13
BE903381A (fr)	1986-04-07
KR870001935B1 (ko)	1987-10-22
JPS61126097A (ja)	1986-06-13
FI853969L (fi)	1986-04-13
SE8504708D0 (sv)	1985-10-11
GB2165539A (en)	1986-04-16
IT8522442A0 (it)	1985-10-11
FI853969A0 (fi)	1985-10-11
FR2571726A1 (fr)	1986-04-18
DD239595A5 (de)	1986-10-01
FI853969A7 (fi)	1986-04-13
PL255741A1 (en)	1986-08-12
DK465585A (da)	1986-04-13
IT1186775B (it)	1987-12-16
DK465585D0 (da)	1985-10-11
HU192472B (en)	1987-06-29
KR860003270A (ko)	1986-05-21
DE3536604A1 (de)	1986-04-17
IL76661A0 (en)	1986-02-28

Legal Events

Date	Code	Title	Description
1988-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
DK170893B1 (da)	1996-03-04	Nye 5'-deoxy-5-fluorcytidinderivater, en fremgangsmåde til fremstilling deraf, farmaceutiske midler indeholdende sådanne derivater og anvendelse af derivaterne til fremstilling af et antitumormiddel
Witkowski et al.	1973	Synthesis and antiviral activity of 1, 2, 4-triazole-3-thiocarboxamide and 1, 2, 4-triazole-3-carboxamidine ribonucleosides
DK170894B1 (da)	1996-03-04	Adenosinderivater, fremgangsmåde til fremstilling deraf, farmaceutiske præparater indeholdende forbindelserne samt anvendelse af forbindelserne
Walton et al.	1969	Branched-chain sugar nucleosides. V. Synthesis and antiviral properties of several branched-chain sugar nucleosides
US4225591A (en)	1980-09-30	2,6-Diaminonebularines
US20210403444A1 (en)	2021-12-30	Heterocyclic derivatives for the treatment of rsv
CN113278040B (zh)	2022-07-05	5’-异丁酰基-n4-羟基胞苷的制备方法
JPH01249797A (ja)	1989-10-05	２’，３’―ジデオキシ―２’，２’―ジフルオロヌクレオシド類
Khodair	2001	Glycosylation of 2-thiohydantoin derivatives. Synthesis of some novel S-alkylated and S-glucosylated hydantoins
US3463850A (en)	1969-08-26	Arabinofuranosyl 2-thiopyrimidines and pharmaceutical compositions thereof
Wempen et al.	1968	Nucleosides. XLVII. Syntheses of some N4-substituted derivatives of 1-. beta.-D-arabinofuranosylcytosine and-5-fluorocytosine
US4341769A (en)	1982-07-27	2,6-Diaminonebularines, their production and use
Ikehara et al.	1965	Studies of Nucleosides and Nucleotides. XXV. Purine Cyclonucleosides. 2. Synthesis of 5'-Deoxyguanosine via an 5', 8-Cyclonucleoside
US4258033A (en)	1981-03-24	2,6-Diaminonebularines
Salvatori et al.	2002	Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1
CS270249B2 (en)	1990-06-13	Method of purine's new derivatives production
EP0356166A2 (de)	1990-02-28	Therapeutische Nucleoside
NL8203476A (nl)	1983-04-05	(e)-5-(2-broomvinyl)uridine, zijn derivaten, alsmede werkwijze voor de bereiding ervan.
NO169962B (no)	1992-05-18	Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrimidinderivater
US3948885A (en)	1976-04-06	5-Hydroxyl-1,2,3-triazole-4-carboxamide nucleoside
RU2187509C1 (ru)	2002-08-20	Производные 5'-h-фосфоната 3'-азидо-3'-дезокситимидина и фармацевтические композиции на их основе
KR870001935B1 (ko)	1987-10-22	항포진성을 갖는 뉴클레오시 유도체 및 그의 산부가염의 제조방법
DEFERRARI et al.	1959	Reaction of Ammonia with Some Acetylated and Benzoylated Monosaccharides. VI. Derivatives of L-Arabinose, D-Xylose, and D-Ribose
US5126347A (en)	1992-06-30	Isomeric dideoxynuclesides
KR0140021B1 (ko)	1998-06-15	피리미딘 아사이클로뉴클레오시드 유도체