PH26589A - Esters of 5-propynyl pyrimidine nucleosides - Google Patents

Esters of 5-propynyl pyrimidine nucleosides Download PDF

Info

Publication number: PH26589A
Authority: PH; Philippines
Prior art keywords: group; represent; prop; arabinofuranosyl; groups
Prior art date: 1988-06-09

Application number

PH38759A

Other languages

English (en)

Inventor

Saad George Rahim

Original Assignee

Wellcome Found

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.)

1988-06-09

Filing date

1989-06-08

Publication date

1992-08-19

1988-06-09 Priority claimed from GB888813680A external-priority patent/GB8813680D0/en

1989-02-21 Priority claimed from GB898903927A external-priority patent/GB8903927D0/en

1989-06-08 Application filed by Wellcome Found filed Critical Wellcome Found

1992-08-19 Publication of PH26589A publication Critical patent/PH26589A/en

Links

150000002148 esters Chemical class 0.000 title claims description 25
239000002718 pyrimidine nucleoside Substances 0.000 title description 4
LMEHJKJEPRYEEB-UHFFFAOYSA-N 5-prop-1-ynylpyrimidine Chemical compound CC#CC1=CN=CN=C1 LMEHJKJEPRYEEB-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 84
239000004480 active ingredient Substances 0.000 claims description 45
-1 tri-phosphate ester Chemical class 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
238000000034 method Methods 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 13
125000001033 ether group Chemical group 0.000 claims description 12
125000004185 ester group Chemical group 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
208000015181 infectious disease Diseases 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000005425 toluyl group Chemical group 0.000 claims description 6
206010015108 Epstein-Barr virus infection Diseases 0.000 claims description 5
208000036142 Viral infection Diseases 0.000 claims description 5
230000000840 anti-viral effect Effects 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
230000009385 viral infection Effects 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
150000001413 amino acids Chemical class 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 3
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
239000001226 triphosphate Substances 0.000 claims description 3
235000011178 triphosphate Nutrition 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 62
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238000003756 stirring Methods 0.000 description 16
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239000008213 purified water Substances 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
238000013375 chromatographic separation Methods 0.000 description 5
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000008569 process Effects 0.000 description 4
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
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HFJMJLXCBVKXNY-IVZWLZJFSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 HFJMJLXCBVKXNY-IVZWLZJFSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
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229940024606 amino acid Drugs 0.000 description 3
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 3
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
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235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229960004906 thiomersal Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
229940100615 topical ointment Drugs 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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
229960004295 valine Drugs 0.000 description 1
210000003501 vero cell Anatomy 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
229960002555 zidovudine Drugs 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
- 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
- C07H19/09—Pyrimidine radicals with arabinosyl as the saccharide radical
- 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)

PH38759A 1988-06-09 1989-06-08 Esters of 5-propynyl pyrimidine nucleosides PH26589A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB888813680A GB8813680D0 (en)	1988-06-09	1988-06-09	Antiviral compounds
GB898903927A GB8903927D0 (en)	1989-02-21	1989-02-21	Antiviral compounds

Publications (1)

Publication Number	Publication Date
PH26589A true PH26589A (en)	1992-08-19

Family

ID=26293991

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH38759A PH26589A (en)	1988-06-09	1989-06-08	Esters of 5-propynyl pyrimidine nucleosides

Country Status (12)

Country	Link
EP (1)	EP0346108A3 (da)
JP (1)	JPH0232094A (da)
KR (1)	KR910000710A (da)
AU (1)	AU614381B2 (da)
DK (1)	DK280089A (da)
FI (1)	FI892820A7 (da)
HU (1)	HU205947B (da)
IL (1)	IL90567A0 (da)
MY (1)	MY106295A (da)
NZ (1)	NZ229457A (da)
PH (1)	PH26589A (da)
PT (1)	PT90788B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8827339D0 (en) *	1988-11-23	1988-12-29	Wellcome Found	Antiviral compounds
WO1991015498A2 (en) *	1990-04-04	1991-10-17	Nycomed Imaging As	Nucleoside derivatives
GB0009486D0 (en)	2000-04-17	2000-06-07	Univ Cardiff	Chemical compounds
EP1525209B1 (en) *	2002-06-28	2017-11-15	Idenix Pharmaceuticals LLC	1'-, 2'- and 3' -modified nucleoside derivatives for treating flaviviridae infections
PT1523489E (pt) *	2002-06-28	2014-06-24	Centre Nat Rech Scient	Profármacos de nucleósido modificado em 2' e 3' para tratamento de infecções por flaviridae
GB0609178D0 (en)	2006-05-09	2006-06-21	Univ Cardiff	Novel compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
GB8517402D0 (en) *	1985-07-10	1985-08-14	Wellcome Found	Treatment of viral infections
GB8629892D0 (en) *	1986-12-15	1987-01-28	Wellcome Found	Antiviral compounds
AU610913B2 (en) *	1987-07-31	1991-05-30	Taiho Pharmaceutical Co., Ltd.	2'-deoxy-5-fluorouridine derivatives
SE8704298D0 (sv) *	1987-11-03	1987-11-03	Astra Ab	Compounds for use in therapy

1989
- 1989-06-07 EP EP19890305774 patent/EP0346108A3/en not_active Withdrawn
- 1989-06-08 FI FI892820A patent/FI892820A7/fi not_active Application Discontinuation
- 1989-06-08 PH PH38759A patent/PH26589A/en unknown
- 1989-06-08 DK DK280089A patent/DK280089A/da not_active Application Discontinuation
- 1989-06-08 NZ NZ229457A patent/NZ229457A/xx unknown
- 1989-06-08 KR KR1019890007969A patent/KR910000710A/ko not_active Ceased
- 1989-06-08 IL IL90567A patent/IL90567A0/xx unknown
- 1989-06-08 HU HU892924A patent/HU205947B/hu not_active IP Right Cessation
- 1989-06-08 AU AU36231/89A patent/AU614381B2/en not_active Ceased
- 1989-06-08 JP JP1146539A patent/JPH0232094A/ja active Pending
- 1989-06-08 PT PT90788A patent/PT90788B/pt not_active IP Right Cessation
- 1989-06-09 MY MYPI89000775A patent/MY106295A/en unknown

Also Published As

Publication number	Publication date
DK280089D0 (da)	1989-06-08
FI892820A0 (fi)	1989-06-08
KR910000710A (ko)	1991-01-30
DK280089A (da)	1989-12-10
MY106295A (en)	1995-04-29
AU3623189A (en)	1989-12-14
NZ229457A (en)	1992-08-26
JPH0232094A (ja)	1990-02-01
HUT52517A (en)	1990-07-28
PT90788B (pt)	1994-11-30
EP0346108A2 (en)	1989-12-13
EP0346108A3 (en)	1991-04-24
PT90788A (pt)	1989-12-29
IL90567A0 (en)	1990-01-18
HU205947B (en)	1992-07-28
AU614381B2 (en)	1991-08-29
FI892820A7 (fi)	1989-12-10

Publication	Publication Date	Title
DK168323B1 (da)	1994-03-14	Anvendelse af visse pyrimidinnucleosider til fremstilling af et lægemiddel mod VZV-infektioner; hidtil ukendte pyrimidinnucleosider, sådanne forbindelser til anvendelse i human terapi samt fremgangsmåde til fremstilling af forbindelserne
DK170803B1 (da)	1996-01-22	2-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-ethyl-L-isoleucinat og salte heraf, disse forbindelsers anvendelse inden for medicinsk terapi, og farmaceutisk komposition indeholdende en sådan forbindelse
US4957924A (en)	1990-09-18	Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof
EP0243670B1 (en)	1992-07-22	Purine and pyrimidine compounds and their use as anti-viral agents
Griengl et al.	1985	5-(Haloalkyl)-2'-deoxyuridines: a novel type of potent antiviral nucleoside analog
PL167317B1 (pl)	1995-08-31	Sposób wytwarzania nowych 4’-tionukleozydów pirymidynowych PL PL
DK171670B1 (da)	1997-03-10	Anvendelse af puriderivater til fremstilling af et lægemiddel til behandling eller forebyggelse af humane virale infektioner forårsaget af VZV, hidtil ukendt 9-beta-D-arabinofuranosyl-2-amino-6-methoxy-9H-purin og derivater heraf, fremgangsmåde til fremstilling af en sådan purinforbindelse og farmaceutisk præparat indeholdende den, samt farmaceutisk acceptabel ester af 9-beta-D-arabino-furanosyl-6
EP0199451A2 (en)	1986-10-29	Therapeutic nucleosides
EP0010205A1 (en)	1980-04-30	5-Substituted 1-(2'-deoxy-2'-substituted-beta-D-arabinofuranosyl) pyrimidine nucleosides and pharmaceutical compositions containing them
KR910008800B1 (ko)	1991-10-21	2'-알킬리덴 피리미딘 누클레오시드 유도체, 그 제조법, 및 그 용도
EP0208550B1 (en)	1991-05-22	Antiviral compounds
NL8005336A (nl)	1981-04-07	E-5-(2-halogeenvinyl)-2'-deoxycytidinen.
US5079252A (en)	1992-01-07	Therapeutic compounds
AU614381B2 (en)	1991-08-29	Esters of 5-alkynyl pyrimidine nucleosides
DE68914750T2 (de)	1994-10-20	Therapeutische Nucleoside.
US5663154A (en)	1997-09-02	2',3'-dideoxy-3'-fluoro-purine ribonucleosides
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
US5028596A (en)	1991-07-02	1-(β-D-arabinofuranosyl)-5-propynyluracil for treatment of VZV infections
EP0375164B1 (en)	1994-04-20	Antiviral compounds
CA2040700A1 (en)	1991-10-19	Antiviral compounds
US5198539A (en)	1993-03-30	5'-esters of 2',3'-dideoxy-3'-fluoro-5-ethynyluridine
US4501744A (en)	1985-02-26	Substituted-aza-cytosine compounds and anti-viral uses thereof
WO1990015064A1 (en)	1990-12-13	Therapeutic nucleosides
JPH05331184A (ja)	1993-12-14	抗ウイルス化合物
JPH0625278A (ja)	1994-02-01	１−（β−Ｄ−エリスロ−ペントフラン−２−ウロシル）ピリミジン誘導体