CA1098036A - Antimicrobial agents and their use - Google Patents

Antimicrobial agents and their use

Info

Publication number: CA1098036A
Authority: CA; Canada
Prior art keywords: ethan; triazol; dichlorophenyl; active ingredient; pharmaceutical composition
Prior art date: 1977-02-11
Legal status (The legal status 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 status listed.): Expired

Application number

CA296,584A

Other languages

English (en)

French (fr)

Inventor

Wolfgang Kramer

Karl H. Buchel

Manfred Plempel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

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.)

1977-02-11

Filing date

1978-02-09

Publication date

1981-03-24

1978-02-09 Application filed by Bayer AG filed Critical Bayer AG

1981-03-24 Application granted granted Critical

1981-03-24 Publication of CA1098036A publication Critical patent/CA1098036A/en

Status Expired legal-status Critical Current

Links

239000004599 antimicrobial Substances 0.000 title abstract description 4
239000003814 drug Substances 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims description 26
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239000003085 diluting agent Substances 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
-1 ampoules Substances 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000003826 tablet Substances 0.000 claims description 6
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150000002367 halogens Chemical class 0.000 claims description 5
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
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239000007788 liquid Substances 0.000 claims description 3
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PSDAPGKSCOCZKG-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(2h-triazol-4-yl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1CC(=O)C1=NNN=C1 PSDAPGKSCOCZKG-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
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RPTCPIUBDIGLOK-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)C(N1N=CN=C1)OC1=CC=C(Cl)C=C1 RPTCPIUBDIGLOK-UHFFFAOYSA-N 0.000 claims 2
NKMZLWXZMMDNLF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(4-phenylphenoxy)-2-(1,2,4-triazol-1-yl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C(N1N=CN=C1)OC1=CC=C(C=2C=CC=CC=2)C=C1 NKMZLWXZMMDNLF-UHFFFAOYSA-N 0.000 claims 1
BNMALZUPMFWQKW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone Chemical group C1=CC(Cl)=CC=C1OC(N1N=CN=C1)C(=O)C1=CC=C(Cl)C=C1Cl BNMALZUPMFWQKW-UHFFFAOYSA-N 0.000 claims 1
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239000003429 antifungal agent Substances 0.000 abstract 1
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239000012433 hydrogen halide Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
230000007775 late Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
239000002304 perfume Substances 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA296,584A 1977-02-11 1978-02-09 Antimicrobial agents and their use Expired CA1098036A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772705679 DE2705679A1 (de)	1977-02-11	1977-02-11	Antimikrobielle mittel
DEP2705679.7		1977-02-11

Publications (1)

Publication Number	Publication Date
CA1098036A true CA1098036A (en)	1981-03-24

Family

ID=6000866

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA296,584A Expired CA1098036A (en)	1977-02-11	1978-02-09	Antimicrobial agents and their use

Country Status (16)

Country	Link
JP (1)	JPS53101537A (de)
AT (1)	AT357154B (de)
AU (1)	AU518192B2 (de)
BE (1)	BE863853A (de)
CA (1)	CA1098036A (de)
CH (1)	CH633185A5 (de)
DE (1)	DE2705679A1 (de)
DK (1)	DK61078A (de)
ES (1)	ES466868A1 (de)
FI (1)	FI780433A7 (de)
FR (1)	FR2380027A1 (de)
GB (1)	GB1560366A (de)
IL (1)	IL54002A (de)
IT (1)	IT7820131A0 (de)
NL (1)	NL7801581A (de)
SE (1)	SE7801528L (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2851086A1 (de) *	1978-11-25	1980-06-04	Bayer Ag	Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2247186A1 (de) *	1972-09-26	1974-03-28	Bayer Ag	Antimykotisches mittel
DE2324424A1 (de) *	1973-05-15	1974-12-05	Bayer Ag	Antimikrobielle mittel

1977
- 1977-02-11 DE DE19772705679 patent/DE2705679A1/de not_active Withdrawn
1978
- 1978-02-02 CH CH117378A patent/CH633185A5/de not_active IP Right Cessation
- 1978-02-07 GB GB4883/78A patent/GB1560366A/en not_active Expired
- 1978-02-09 FI FI780433A patent/FI780433A7/fi not_active Application Discontinuation
- 1978-02-09 SE SE7801528A patent/SE7801528L/xx unknown
- 1978-02-09 JP JP1306078A patent/JPS53101537A/ja active Pending
- 1978-02-09 IT IT7820131A patent/IT7820131A0/it unknown
- 1978-02-09 IL IL54002A patent/IL54002A/xx unknown
- 1978-02-09 CA CA296,584A patent/CA1098036A/en not_active Expired
- 1978-02-10 DK DK61078A patent/DK61078A/da unknown
- 1978-02-10 FR FR7803832A patent/FR2380027A1/fr active Granted
- 1978-02-10 ES ES466868A patent/ES466868A1/es not_active Expired
- 1978-02-10 BE BE185070A patent/BE863853A/xx unknown
- 1978-02-10 NL NL7801581A patent/NL7801581A/xx not_active Application Discontinuation
- 1978-02-10 AT AT94578A patent/AT357154B/de not_active IP Right Cessation
- 1978-02-13 AU AU33244/78A patent/AU518192B2/en not_active Expired

Also Published As

Publication number	Publication date
FI780433A7 (fi)	1978-08-12
BE863853A (fr)	1978-08-10
ATA94578A (de)	1979-11-15
FR2380027A1 (fr)	1978-09-08
FR2380027B1 (de)	1980-07-04
GB1560366A (en)	1980-02-06
IT7820131A0 (it)	1978-02-09
DK61078A (da)	1978-08-12
ES466868A1 (es)	1978-10-01
IL54002A (en)	1982-04-30
SE7801528L (sv)	1978-08-12
AT357154B (de)	1980-06-25
DE2705679A1 (de)	1978-08-17
NL7801581A (nl)	1978-08-15
IL54002A0 (en)	1978-04-30
AU3324478A (en)	1979-08-23
JPS53101537A (en)	1978-09-05
CH633185A5 (en)	1982-11-30
AU518192B2 (en)	1981-09-17

Legal Events

Date	Code	Title	Description
1998-03-24	MKEX	Expiry

Publication	Publication Date	Title
CA1128528A (en)	1982-07-27	Hydroxyethyl-azole compounds, their production and their medicinal use
US3812142A (en)	1974-05-21	Imidazolyl ketones
JPH0222731B2 (de)	1990-05-21
US4233311A (en)	1980-11-11	Antimicrobial agents and their use
IE48880B1 (en)	1985-06-12	New hydroxypropyl-triazole compounds,their production and their medicinal use
US5011850A (en)	1991-04-30	Substituted diazolylalkyl-carbinols, a process for their preparation and their use as antimycotic agents
US4910213A (en)	1990-03-20	Antimycotic agents
US4215131A (en)	1980-07-29	Antimicrobial agents
US4894382A (en)	1990-01-16	Substituted 1,3-diazolyl-2-propanols and their use as antimycotic agents
IL44794A (en)	1977-08-31	Antimicrobial compositions containing certain 1,2,4-or 1,2,3-triazolyl o,n-acetal derivatives
US4489085A (en)	1984-12-18	Antimicrobial agents and their use employing imidazolyl-enal ethers
CA1098036A (en)	1981-03-24	Antimicrobial agents and their use
GB1564371A (en)	1980-04-10	Antimicrobial agents containing imidazole derivatives
CA1160237A (en)	1984-01-10	Biphenylyl-azolylethane compounds, their production and their medicinal use
IL45771A (en)	1977-11-30	Pharmaceutical compositions containing 1-(2-phenoxy-3-hydroxy-alkyl)-1,2,4-triazole derivatives
US5126359A (en)	1992-06-30	Substituted bisazoles and their use as medicaments
US4239765A (en)	1980-12-16	Fluorenyl-azolylmethyl-carbinol compounds and their medicinal use
HU193278B (en)	1987-09-28	Process for production of derivatives of triasole with antifungicide effect and medical preparatives containing thereof
JPS6030290B2 (ja)	1985-07-16	製薬組成物及び使用
JPH0456035B2 (de)	1992-09-07
US4207328A (en)	1980-06-10	1-Phenoxy-2-(2,4-dichlorophenyl)-1-imidazol-1-yl-ethan-2-ones and -ols and antimycotic and fungicidal use
CA1097356A (en)	1981-03-10	2,4-dichlorophenyl-imidazolyl-ethan-ones and -ols, a process for their preparation and their use as medicaments
US4418072A (en)	1983-11-29	Diastereomeric 1-(4-chlorophenoxy)-1-(1-imidazolyl)-3,3-dimethyl-2-butanol compounds and their antimycotic use
CA1232909A (en)	1988-02-16	1,2,4-triazolylpropanols, and their production and use
IL45672A (en)	1977-06-30	Anti-microbial compositions containing 1-(1,2,4-triazol-1-yl)-2-phenoxy-4,4-dimethyl-pentan-3-one derivatives