OA10579A - Flavin derivatives as anti-viral agents - Google Patents

Flavin derivatives as anti-viral agents Download PDF

Info

Publication number: OA10579A
Authority: OA; OAPI
Prior art keywords: flavin; hydrogen; dérivative; compound; alkyl
Prior art date: 1993-10-19

Application number

OA60815A

Other languages

English (en)

Inventor

Washington Osur Ayuko

Original Assignee

Radopath Ltd

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.)

1993-10-19

Filing date

1996-04-18

Publication date

2002-06-19

1996-04-18 Application filed by Radopath Ltd filed Critical Radopath Ltd

2002-06-19 Publication of OA10579A publication Critical patent/OA10579A/en

Links

150000002211 flavins Chemical class 0.000 title abstract description 5
239000003443 antiviral agent Substances 0.000 title abstract description 4
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims abstract description 59
235000019192 riboflavin Nutrition 0.000 claims abstract description 28
239000002151 riboflavin Substances 0.000 claims abstract description 28
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 claims abstract description 27
229960002477 riboflavin Drugs 0.000 claims abstract description 27
150000001875 compounds Chemical class 0.000 claims description 45
208000015181 infectious disease Diseases 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 18
238000002560 therapeutic procedure Methods 0.000 claims description 14
230000037396 body weight Effects 0.000 claims description 11
ZJTJUVIJVLLGSP-UHFFFAOYSA-N lumichrome Chemical compound N1C(=O)NC(=O)C2=C1N=C1C=C(C)C(C)=CC1=N2 ZJTJUVIJVLLGSP-UHFFFAOYSA-N 0.000 claims description 10
KPDQZGKJTJRBGU-UHFFFAOYSA-N lumiflavin Chemical compound CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O KPDQZGKJTJRBGU-UHFFFAOYSA-N 0.000 claims description 8
FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 claims description 6
208000036142 Viral infection Diseases 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
230000009385 viral infection Effects 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
HAUGRYOERYOXHX-UHFFFAOYSA-N Alloxazine Chemical compound C1=CC=C2N=C(C(=O)NC(=O)N3)C3=NC2=C1 HAUGRYOERYOXHX-UHFFFAOYSA-N 0.000 claims description 3
208000031886 HIV Infections Diseases 0.000 claims description 3
208000037357 HIV infectious disease Diseases 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 10
229910052739 hydrogen Inorganic materials 0.000 claims 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 6
125000001475 halogen functional group Chemical group 0.000 claims 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
229910052757 nitrogen Inorganic materials 0.000 claims 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
238000011321 prophylaxis Methods 0.000 claims 2
206010011416 Croup infectious Diseases 0.000 claims 1
241001043916 Saitis Species 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
201000010549 croup Diseases 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
229950001574 riboflavin phosphate Drugs 0.000 claims 1
150000003568 thioethers Chemical class 0.000 claims 1
150000003287 riboflavins Chemical class 0.000 abstract 1
210000004027 cell Anatomy 0.000 description 29
238000003556 assay Methods 0.000 description 27
FCASKLHVRFDIJB-UHFFFAOYSA-N Riboflavine Natural products Cc1cc2N=C3C(NC(=O)NC3=O)N(CC(O)C(O)C(O)CO)c2cc1C FCASKLHVRFDIJB-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 12
230000001154 acute effect Effects 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000000034 method Methods 0.000 description 9
238000012289 standard assay Methods 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 7
231100000419 toxicity Toxicity 0.000 description 6
230000001988 toxicity Effects 0.000 description 6
241000700605 Viruses Species 0.000 description 5
239000000427 antigen Substances 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
238000004113 cell culture Methods 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
230000003612 virological effect Effects 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
230000000840 anti-viral effect Effects 0.000 description 4
230000030833 cell death Effects 0.000 description 4
239000012737 fresh medium Substances 0.000 description 4
238000011533 pre-incubation Methods 0.000 description 4
229940088594 vitamin Drugs 0.000 description 4
235000013343 vitamin Nutrition 0.000 description 4
239000011782 vitamin Substances 0.000 description 4
229930003231 vitamin Natural products 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
210000000805 cytoplasm Anatomy 0.000 description 3
238000009472 formulation Methods 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
230000001052 transient effect Effects 0.000 description 3
210000002845 virion Anatomy 0.000 description 3
-1 vitamin vitamin Chemical class 0.000 description 3
229910014033 C-OH Inorganic materials 0.000 description 2
101710132601 Capsid protein Proteins 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
210000001744 T-lymphocyte Anatomy 0.000 description 2
201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000010627 oxidative phosphorylation Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
229910000162 sodium phosphate Inorganic materials 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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 2
229960002555 zidovudine Drugs 0.000 description 2
208000030507 AIDS Diseases 0.000 description 1
101150097308 ARD1 gene Proteins 0.000 description 1
102100038740 Activator of RNA decay Human genes 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
229930024421 Adenine Natural products 0.000 description 1
241000726103 Atta Species 0.000 description 1
108020004414 DNA Proteins 0.000 description 1
102000053602 DNA Human genes 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
101100270214 Dictyostelium discoideum natA gene Proteins 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
241000950314 Figura Species 0.000 description 1
VWWQXMAJTJZDQX-UHFFFAOYSA-N Flavine adenine dinucleotide Natural products C1=NC2=C(N)N=CN=C2N1C(C(O)C1O)OC1COP(O)(=O)OP(O)(=O)OCC(O)C(O)C(O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UHFFFAOYSA-N 0.000 description 1
208000005577 Gastroenteritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000282412 Homo Species 0.000 description 1
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 description 1
241001465754 Metazoa Species 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
108010003533 Viral Envelope Proteins Proteins 0.000 description 1
108020000999 Viral RNA Proteins 0.000 description 1
208000007642 Vitamin B Deficiency Diseases 0.000 description 1
206010000059 abdominal discomfort Diseases 0.000 description 1
206010000269 abscess Diseases 0.000 description 1
229960000643 adenine Drugs 0.000 description 1
230000002411 adverse Effects 0.000 description 1
208000026802 afebrile Diseases 0.000 description 1
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
229960003022 amoxicillin Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
230000036528 appetite Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
238000009640 blood culture Methods 0.000 description 1
244000309466 calf Species 0.000 description 1
235000019577 caloric intake Nutrition 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
230000033077 cellular process Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000013611 chromosomal DNA Substances 0.000 description 1
210000000349 chromosome Anatomy 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
235000018823 dietary intake Nutrition 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000027950 fever generation Effects 0.000 description 1
VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
230000006525 intracellular process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000009533 lab test Methods 0.000 description 1
206010025482 malaise Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
210000004779 membrane envelope Anatomy 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
238000006241 metabolic reaction Methods 0.000 description 1
229960000988 nystatin Drugs 0.000 description 1
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000003319 supportive effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000002723 toxicity assay Methods 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1

Classifications

- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/525—Isoalloxazines, e.g. riboflavins, vitamin B2
- 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- 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

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Molecular Biology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA60815A 1993-10-19 1996-04-18 Flavin derivatives as anti-viral agents OA10579A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939321558A GB9321558D0 (en)	1993-10-19	1993-10-19	Anti-viral agents

Publications (1)

Publication Number	Publication Date
OA10579A true OA10579A (en)	2002-06-19

Family

ID=10743784

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60815A OA10579A (en)	1993-10-19	1996-04-18	Flavin derivatives as anti-viral agents

Country Status (26)

Country	Link
EP (1)	EP0739208A1 (ru)
JP (1)	JPH09505804A (ru)
CN (1)	CN1140992A (ru)
AP (1)	AP620A (ru)
AU (1)	AU7943794A (ru)
BG (1)	BG100599A (ru)
BR (1)	BR9407862A (ru)
CA (2)	CA2123825A1 (ru)
CO (1)	CO4520283A1 (ru)
CZ (1)	CZ113796A3 (ru)
EE (1)	EE9600057A (ru)
GB (2)	GB9321558D0 (ru)
HR (1)	HRP940688A2 (ru)
HU (1)	HUT76322A (ru)
IL (1)	IL111338A0 (ru)
JO (1)	JO1866B1 (ru)
MA (1)	MA23356A1 (ru)
MD (1)	MD960168A (ru)
NO (1)	NO961547L (ru)
OA (1)	OA10579A (ru)
PE (1)	PE5596A1 (ru)
PL (1)	PL314008A1 (ru)
SK (1)	SK50696A3 (ru)
UY (1)	UY23844A1 (ru)
WO (1)	WO1995011028A1 (ru)
ZA (1)	ZA948191B (ru)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07188052A (ja) *	1993-12-27	1995-07-25	Sanwa Kagaku Kenkyusho Co Ltd	インターフェロン用作用効果増強剤及び該増強剤とインターフェロンとを含有する抗ウイルス活性増強組成物
US5756479A (en) *	1994-12-29	1998-05-26	Research Development Foundation	Flavin adenine dinucleotide analogue inhibitors of monoamine oxidase
US7049110B2 (en)	1998-07-21	2006-05-23	Gambro, Inc.	Inactivation of West Nile virus and malaria using photosensitizers
US7498156B2 (en)	1998-07-21	2009-03-03	Caridianbct Biotechnologies, Llc	Use of visible light at wavelengths of 500 to 550 nm to reduce the number of pathogens in blood and blood components
US7094378B1 (en)	2000-06-15	2006-08-22	Gambro, Inc.	Method and apparatus for inactivation of biological contaminants using photosensitizers
US7220747B2 (en)	1999-07-20	2007-05-22	Gambro, Inc.	Method for preventing damage to or rejuvenating a cellular blood component using mitochondrial enhancer
US9044523B2 (en)	2000-06-15	2015-06-02	Terumo Bct, Inc.	Reduction of contaminants in blood and blood products using photosensitizers and peak wavelengths of light
US6933285B2 (en) *	2002-05-10	2005-08-23	The Ohio State University	Flavin N-oxides: new anti-cancer agents and pathogen eradication agents
ITTO20020622A1 (it)	2002-07-16	2004-01-16	Dayco Europe Srl	Gruppo integrato puleggia-smorzatore torsionale
WO2004013142A1 (en) *	2002-08-02	2004-02-12	The Institute Of Radiation Medicine, Academy Of Miilitary Medical Sciences, People's Liberation Army	A riboflavin derivative and its manufacture and uses
EP2545788A1 (de) *	2011-07-13	2013-01-16	Martin Hulliger	Diätisches Mehrkomponentensystem
JP2018131410A (ja) *	2017-02-15	2018-08-23	ヒノキ新薬株式会社	カスパーゼ−３阻害剤とその用途
JP2021500374A (ja) *	2017-10-24	2021-01-07	ルネラ・バイオテック・インコーポレーテッド	標的フラビン含有酵素がミトコンドリア呼吸を阻害することにより癌幹細胞（ｃｓｃｓ）を排除するミトフラボスチン
US20220257550A1 (en) *	2019-07-09	2022-08-18	Dsm Ip Assets B.V.	Reducing the viral activity of elafibranor with riboflavin or dha

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4219545A (en) *	1979-03-23	1980-08-26	Collins Calvin E	Treatment of infectious keratoconjunctivitis in animals
US4264601A (en) *	1979-06-12	1981-04-28	The Board Of Regents Of The University Of Oklahoma	Antihypertensive agents and their use in treatment of hypertension
US4500524A (en) *	1982-09-15	1985-02-19	Trustees Of Boston University	Tranquilizing and reducing or preventing seizures
WO1991002529A2 (en) *	1989-08-14	1991-03-07	John Bennett Kizer	Product and method for killing abnormal vertebrate cells
JP2727471B2 (ja) *	1989-09-14	1998-03-11	三井農林株式会社	インフルエンザウィルス感染予防剤
US5192264A (en) *	1989-10-06	1993-03-09	The Beth Israel Hospital Association	Methods and apparatus for treating disease states using oxidized lipoproteins
US5217716A (en) *	1990-07-18	1993-06-08	The Beth Israel Hospital Association	Method for treating viral infections using oxidized lipoproteins
FR2674753B1 (fr) *	1991-04-02	1995-03-10	Jean Berque	Nouvelles indications therapeutiques, en particulier pour le traitement du sida, d'un medicament deja existant et fabrique a partir d'une molecule denuee de contre-indications et d'effets indesirables.
NZ244270A (en) *	1991-09-13	1995-07-26	Eisai Co Ltd	Injectable composition comprising riboflavin
AU3222893A (en) *	1991-11-25	1993-06-28	University Of Michigan, The	Therapeutic composition and method for preventing reperfusion injury
JP3073309B2 (ja) *	1992-03-27	2000-08-07	雪印乳業株式会社	シアル酸結合５−デアザフラビン系化合物

1993
- 1993-10-19 GB GB939321558A patent/GB9321558D0/en active Pending
1994
- 1994-01-19 JO JO19941866A patent/JO1866B1/en active
- 1994-05-18 CA CA2123825A patent/CA2123825A1/en active Pending
- 1994-10-18 MA MA23679A patent/MA23356A1/fr unknown
- 1994-10-19 HR HR9321558.0A patent/HRP940688A2/hr not_active Application Discontinuation
- 1994-10-19 CZ CZ961137A patent/CZ113796A3/cs unknown
- 1994-10-19 ZA ZA948191A patent/ZA948191B/xx unknown
- 1994-10-19 WO PCT/GB1994/002292 patent/WO1995011028A1/en not_active Ceased
- 1994-10-19 PE PE1994253128A patent/PE5596A1/es not_active Application Discontinuation
- 1994-10-19 PL PL94314008A patent/PL314008A1/xx unknown
- 1994-10-19 GB GB9421099A patent/GB2283913A/en not_active Withdrawn
- 1994-10-19 CA CA002174552A patent/CA2174552A1/en not_active Abandoned
- 1994-10-19 HU HU9601006A patent/HUT76322A/hu unknown
- 1994-10-19 BR BR9407862A patent/BR9407862A/pt not_active Application Discontinuation
- 1994-10-19 AU AU79437/94A patent/AU7943794A/en not_active Abandoned
- 1994-10-19 EP EP94930272A patent/EP0739208A1/en not_active Withdrawn
- 1994-10-19 EE EE9600057A patent/EE9600057A/xx unknown
- 1994-10-19 SK SK506-96A patent/SK50696A3/sk unknown
- 1994-10-19 IL IL11133894A patent/IL111338A0/xx unknown
- 1994-10-19 CO CO94047671A patent/CO4520283A1/es unknown
- 1994-10-19 CN CN94194350A patent/CN1140992A/zh active Pending
- 1994-10-19 JP JP7511518A patent/JPH09505804A/ja active Pending
- 1994-10-19 UY UY23844A patent/UY23844A1/es unknown
- 1994-10-19 AP APAP/P/1994/000695A patent/AP620A/en active
1996
- 1996-04-18 NO NO961547A patent/NO961547L/no unknown
- 1996-04-18 OA OA60815A patent/OA10579A/en unknown
- 1996-05-17 BG BG100599A patent/BG100599A/xx unknown
- 1996-05-17 MD MD96-0168A patent/MD960168A/ru not_active Application Discontinuation

Also Published As

Publication number	Publication date
AP620A (en)	1997-10-14
UY23844A1 (es)	1995-03-28
JPH09505804A (ja)	1997-06-10
GB9421099D0 (en)	1994-12-07
EE9600057A (et)	1996-10-15
IL111338A0 (en)	1994-12-29
WO1995011028A1 (en)	1995-04-27
EP0739208A1 (en)	1996-10-30
GB9321558D0 (en)	1993-12-08
MD960168A (ru)	1998-04-30
HRP940688A2 (en)	1997-04-30
NO961547L (no)	1996-06-19
PL314008A1 (en)	1996-08-05
CZ113796A3 (en)	1996-11-13
JO1866B1 (en)	1995-12-27
CO4520283A1 (es)	1997-10-15
CA2174552A1 (en)	1995-04-27
HUT76322A (en)	1997-08-28
AP9400695A0 (en)	1995-01-31
GB2283913A (en)	1995-05-24
PE5596A1 (es)	1996-04-18
HU9601006D0 (en)	1996-06-28
SK50696A3 (en)	1997-01-08
ZA948191B (en)	1995-06-08
BR9407862A (pt)	1997-05-20
BG100599A (en)	1997-02-28
MA23356A1 (fr)	1995-07-01
CA2123825A1 (en)	1995-04-20
NO961547D0 (no)	1996-04-18
AU7943794A (en)	1995-05-08
CN1140992A (zh)	1997-01-22

Publication	Publication Date	Title
OA10579A (en)	2002-06-19	Flavin derivatives as anti-viral agents
CA2032261C (en)	2002-04-23	Antiviral polyheterocyclic dimers
EP1095042B9 (en)	2006-07-05	Antiparasitic artemisinin derivatives (endoperoxides)
US20070054876A1 (en)	2007-03-08	Pharmaceutical composition promoting defecation
US4898870A (en)	1990-02-06	Pyrroloquinoline quinone compounds useful as an enzyme inhibitor
US20040259865A1 (en)	2004-12-23	Pyrimidone compounds and pharmaceutical compositions containing the same
EP4277631A1 (en)	2023-11-22	Azaquinazoline derivatives for use in treating or preventing dirofilaria infection in a mammal
US5962480A (en)	1999-10-05	Drug for ameliorating brain diseases
JP4553569B2 (ja)	2010-09-29	フェノール系誘導体を有効成分とするクリプトスポリジウム症の予防・治療剤
PT99434A (pt)	1992-09-30	Processo para a preparacao de composicoes farmaceuticas contendo derivados de xantina
US20210369699A1 (en)	2021-12-02	Treatment of lupus erythematosus using s-hydroxychloroquine
NZ217431A (en)	1990-01-29	Synergistically antimalarial combination preparations comprising an iron(iii) chelating agent and a schizontocide
KR0133555B1 (ko)	1998-04-23	5-플루오로우라실계 화합물에 기인한 염증의 발생을 억제할 수 있는 비-주사제 형태의 항암조성물
NZ755175A (en)	2021-07-30	Monoterpene phenol derivatives
KR20080071182A (ko)	2008-08-01	9-옥소아크리딘-10-아세트산 및 1-알킬아미노-1-데옥시폴리올의 염, 이들을 포함하는 약학적 조성물 및 치료 방법
EP0476391B1 (en)	1996-04-10	Anti-AIDS virus composition containing cepharanthine as active compound
CN117715908A (zh)	2024-03-15	具有整合酶抑制活性的吡啶酮化合物及其药用用途
GB2319474A (en)	1998-05-27	Anti-viral agents
IL44124A (en)	1977-10-31	Compositions containing 2-amino-4-hydroxy-7,8-dihydro pteridine derivatives for treating microbial infections
Prochaska et al.	1995	Inhibition of human immunodeficiency virus type 1 replication by 7-methyl-6, 8-bis (methylthio) pyrrolo [1, 2-a] pyrazine, an in vivo metabolite of oltipraz.
KR100532542B1 (ko)	2005-12-01	아르세닉산, 메타아르세나이트 또는 이들의 약제학적허용가능한 염을 함유한 에이즈 예방 및 치료용 약제 조성물
AU629520B2 (en)	1992-10-08	A medicament
JPS624366B2 (ru)	1987-01-30
KR20020078202A (ko)	2002-10-18	알로에신을 함유하는 허혈성 질환의 예방 및 치료용조성물, 및 이를 포함하는 제제
JP2001081029A (ja)	2001-03-27	テロメラーゼ阻害剤