HUT73779A - Method of combating acyclovir-resistant herpes simplex viral infections - Google Patents

Method of combating acyclovir-resistant herpes simplex viral infections Download PDF

Info

Publication number: HUT73779A
Authority: HU; Hungary
Prior art keywords: carbamoyl; butyl; ethyl; cme; group
Prior art date: 1993-05-03

Application number

HU9503135A

Other languages

English (en)

Hungarian (hu)

Other versions

HU9503135D0 (en

Inventor

James Gus Chafouleas

Robert Deziel

Original Assignee

Bio Mega Boehringer Ingelheim

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.)

1993-05-03

Filing date

1994-04-29

Publication date

1996-09-30

1994-04-29 Application filed by Bio Mega Boehringer Ingelheim filed Critical Bio Mega Boehringer Ingelheim

1996-01-29 Publication of HU9503135D0 publication Critical patent/HU9503135D0/hu

1996-09-30 Publication of HUT73779A publication Critical patent/HUT73779A/hu

Links

MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 title claims description 76
229960004150 aciclovir Drugs 0.000 title claims description 74
208000009889 Herpes Simplex Diseases 0.000 title claims description 10
208000036142 Viral infection Diseases 0.000 title claims 2
230000009385 viral infection Effects 0.000 title claims 2
238000000034 method Methods 0.000 title description 39
-1 phenylacetyl Chemical group 0.000 claims description 189
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150000001875 compounds Chemical class 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
229910052799 carbon Inorganic materials 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
230000000840 anti-viral effect Effects 0.000 claims description 26
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 23
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
150000001721 carbon Chemical group 0.000 claims description 21
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
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238000011282 treatment Methods 0.000 claims description 18
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
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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
238000004128 high performance liquid chromatography Methods 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000010410 layer Substances 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
238000013048 microbiological method Methods 0.000 description 1
238000002941 microtiter virus yield reduction assay Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
208000025113 myeloid leukemia Diseases 0.000 description 1
PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
ABNHCYDWRNRPJO-UHFFFAOYSA-N phenylmethoxymethylbenzene;hydrochloride Chemical compound Cl.C=1C=CC=CC=1COCC1=CC=CC=C1 ABNHCYDWRNRPJO-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011552 rat model Methods 0.000 description 1
230000008261 resistance mechanism Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000011894 semi-preparative HPLC Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
230000037351 starvation Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FMXIVGMLPNOZDE-VIFPVBQESA-N tert-butyl n-[(2s)-1-hydroxy-4,4-dimethylpentan-2-yl]carbamate Chemical compound CC(C)(C)C[C@@H](CO)NC(=O)OC(C)(C)C FMXIVGMLPNOZDE-VIFPVBQESA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000009210 therapy by ultrasound Methods 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
239000001226 triphosphate Substances 0.000 description 1
235000011178 triphosphate Nutrition 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
229960004295 valine Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000007442 viral DNA synthesis Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- 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
- A61K31/52—Purines, e.g. adenine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- 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
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Virology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Immunology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Gastroenterology & Hepatology (AREA)
Biotechnology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

HU9503135A 1993-05-03 1994-04-29 Method of combating acyclovir-resistant herpes simplex viral infections HUT73779A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002095408A CA2095408A1 (en)	1993-05-03	1993-05-03	Method of combating acyclovir-resistant herpes simplex viral infections

Publications (2)

Publication Number	Publication Date
HU9503135D0 HU9503135D0 (en)	1996-01-29
HUT73779A true HUT73779A (en)	1996-09-30

Family

ID=4151571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9503135A HUT73779A (en)	1993-05-03	1994-04-29	Method of combating acyclovir-resistant herpes simplex viral infections

Country Status (13)

Country	Link
EP (1)	EP0767671A1 (cs)
JP (1)	JPH08509476A (cs)
KR (1)	KR960701651A (cs)
CN (1)	CN1126438A (cs)
AU (1)	AU683465B2 (cs)
BR (1)	BR9406575A (cs)
CA (1)	CA2095408A1 (cs)
CZ (1)	CZ287795A3 (cs)
HU (1)	HUT73779A (cs)
NO (1)	NO954390L (cs)
SG (1)	SG48806A1 (cs)
SK (1)	SK132695A3 (cs)
WO (1)	WO1994025046A1 (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6599887B2 (en)	1988-07-07	2003-07-29	Chimerix, Inc.	Methods of treating viral infections using antiviral liponucleotides
US6252060B1 (en)	1988-07-07	2001-06-26	Nexstar Pharmaceuticals, Inc.	Antiviral liponucleosides: treatment of hepatitis B
US5817638A (en) *	1988-07-07	1998-10-06	Nexstar Pharmaceuticals, Inc.	Antiviral liponucleosides: treatment of hepatitis B
CA2230750C (en) *	1994-12-28	2002-05-21	Boehringer Ingelheim (Canada) Ltd./ Boehringer Ingelheim (Canada) Ltee	Antiherpes peptidomimetic compounds
CN109627243B (zh) *	2019-01-09	2021-06-29	广西壮族自治区水产科学研究院	一种喷昔洛韦-铜配合物、合成方法及其应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2033448C (en) *	1990-12-31	1996-11-26	Boehringer Ingelheim (Canada) Ltd./ Boehringer Ingelheim (Canada) Ltee	Antiherpes compositions and method of use
DE69320390T2 (de) *	1992-03-12	1999-02-11	Boehringer Ingelheim (Canada) Ltd., Laval, Quebec	Isosterische Peptidderivate gegen Herpes

1993
- 1993-05-03 CA CA002095408A patent/CA2095408A1/en not_active Abandoned
1994
- 1994-04-29 AU AU66423/94A patent/AU683465B2/en not_active Expired - Fee Related
- 1994-04-29 CZ CZ952877A patent/CZ287795A3/cs unknown
- 1994-04-29 SG SG1996001910A patent/SG48806A1/en unknown
- 1994-04-29 WO PCT/CA1994/000242 patent/WO1994025046A1/en not_active Ceased
- 1994-04-29 KR KR1019950704828A patent/KR960701651A/ko not_active Withdrawn
- 1994-04-29 HU HU9503135A patent/HUT73779A/hu unknown
- 1994-04-29 CN CN94192662A patent/CN1126438A/zh active Pending
- 1994-04-29 BR BR9406575A patent/BR9406575A/pt not_active Application Discontinuation
- 1994-04-29 JP JP6523705A patent/JPH08509476A/ja active Pending
- 1994-04-29 EP EP94914991A patent/EP0767671A1/en not_active Ceased
- 1994-04-29 SK SK1326-95A patent/SK132695A3/sk unknown
1995
- 1995-11-02 NO NO954390A patent/NO954390L/no unknown

Also Published As

Publication number	Publication date
HU9503135D0 (en)	1996-01-29
AU683465B2 (en)	1997-11-13
NO954390L (no)	1996-01-02
JPH08509476A (ja)	1996-10-08
NO954390D0 (no)	1995-11-02
CZ287795A3 (en)	1996-06-12
SK132695A3 (en)	1996-10-02
AU6642394A (en)	1994-11-21
KR960701651A (ko)	1996-03-28
BR9406575A (pt)	1996-03-19
EP0767671A1 (en)	1997-04-16
CA2095408A1 (en)	1994-11-04
WO1994025046A1 (en)	1994-11-10
SG48806A1 (en)	1998-05-18
CN1126438A (zh)	1996-07-10

Legal Events

Date	Code	Title	Description
1997-09-29	DGB9	Succession in title of applicant	Owner name: BOEHRINGER INGELHEIM (CANADA) LTD., CA
1999-01-28	DFD9	Temporary protection cancelled due to non-payment of fee

Publication	Publication Date	Title
JP3209553B2 (ja)	2001-09-17	ヘルペス感染治療用医薬組成物
JP3209552B2 (ja)	2001-09-17	ヘルペス感染治療用医薬組成物
HUT73779A (en)	1996-09-30	Method of combating acyclovir-resistant herpes simplex viral infections
HU211926A9 (en)	1996-01-29	Izosteric antiherpes peptide derivatives
AU683450B2 (en)	1997-11-13	Inhibitors of herpes viral ribonucleotide reductase
US5574015A (en)	1996-11-12	Isosteric antiherpes peptide derivatives
DE69319266T2 (de)	1998-11-26	Peptidderivate mit einem Ureido-N-Terminus gegen Herpes
AU671825C (en)	1997-02-20	Isosteric antiherpes peptide derivatives
EP0837845B1 (en)	2001-11-28	Herpes ribonucleotide reductase inhibitors