CH646948A5 - Chlorhexidinsalze und praeparate enthaltend dieselben. - Google Patents

Chlorhexidinsalze und praeparate enthaltend dieselben. Download PDF

Info

Publication number: CH646948A5
Authority: CH; Switzerland
Prior art keywords: preparation; acid; compound; amount; chlorhexidine
Prior art date: 1979-04-26

Application number

CH322480A

Other languages

German (de)

English (en)

Inventor

Paul L Jun Warner

Grey B Kornegay

George Redl

Original Assignee

Bristol Myers Co

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.)

1979-04-26

Filing date

1980-04-25

Publication date

1984-12-28

1980-04-25 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1984-12-28 Publication of CH646948A5 publication Critical patent/CH646948A5/de

Links

GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical class C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 title claims description 80
238000002360 preparation method Methods 0.000 title claims description 52
229960003260 chlorhexidine Drugs 0.000 claims description 74
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical group C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 43
229960000210 nalidixic acid Drugs 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
OAOBMEMWHJWPNA-UHFFFAOYSA-N (4-aminophenyl)phosphonic acid Chemical group NC1=CC=C(P(O)(O)=O)C=C1 OAOBMEMWHJWPNA-UHFFFAOYSA-N 0.000 claims description 19
235000010199 sorbic acid Nutrition 0.000 claims description 17
239000004334 sorbic acid Substances 0.000 claims description 17
229940075582 sorbic acid Drugs 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
230000000844 anti-bacterial effect Effects 0.000 claims description 14
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
150000004682 monohydrates Chemical class 0.000 claims description 7
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
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238000004519 manufacturing process Methods 0.000 claims description 4
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150000007513 acids Chemical class 0.000 claims description 2
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210000003608 fece Anatomy 0.000 claims 2
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150000003839 salts Chemical class 0.000 description 28
238000002156 mixing Methods 0.000 description 22
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
238000009472 formulation Methods 0.000 description 18
239000002585 base Substances 0.000 description 12
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
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244000038458 Nepenthes mirabilis Species 0.000 description 8
241000588777 Providencia rettgeri Species 0.000 description 8
RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
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244000110797 Polygonum persicaria Species 0.000 description 7
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WDRFFJWBUDTUCA-UHFFFAOYSA-N chlorhexidine acetate Chemical compound CC(O)=O.CC(O)=O.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WDRFFJWBUDTUCA-UHFFFAOYSA-N 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000607715 Serratia marcescens Species 0.000 description 6
229960001884 chlorhexidine diacetate Drugs 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
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239000004310 lactic acid Substances 0.000 description 5
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241000194017 Streptococcus Species 0.000 description 4
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 3
150000008043 acidic salts Chemical class 0.000 description 3
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229920006007 hydrogenated polyisobutylene Polymers 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
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YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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229920002125 Sokalan® Polymers 0.000 description 2
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PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
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CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
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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
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 description 1
QPCDCPDFJACHGM-UHFFFAOYSA-K pentetate(3-) Chemical compound OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O QPCDCPDFJACHGM-UHFFFAOYSA-K 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003212 purines Chemical class 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
230000035945 sensitivity Effects 0.000 description 1
229960003339 sodium phosphate Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
JDVPQXZIJDEHAN-UHFFFAOYSA-M succinamate Chemical compound NC(=O)CCC([O-])=O JDVPQXZIJDEHAN-UHFFFAOYSA-M 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940072172 tetracycline antibiotic Drugs 0.000 description 1
230000000699 topical effect Effects 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
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
- C07C279/265—X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/10—Sorbic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

CH322480A 1979-04-26 1980-04-25 Chlorhexidinsalze und praeparate enthaltend dieselben. CH646948A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3359379A	1979-04-26	1979-04-26

Publications (1)

Publication Number	Publication Date
CH646948A5 true CH646948A5 (de)	1984-12-28

Family

ID=21871298

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH322480A CH646948A5 (de)	1979-04-26	1980-04-25	Chlorhexidinsalze und praeparate enthaltend dieselben.
CH3086/84A CH648755A5 (de)	1979-04-26	1980-04-25	Chlorhexidin enthaltende synergistische praeparate zur verhinderung des wachstums von mikroorganismen.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH3086/84A CH648755A5 (de)	1979-04-26	1980-04-25	Chlorhexidin enthaltende synergistische praeparate zur verhinderung des wachstums von mikroorganismen.

Country Status (13)

Country	Link
JP (1)	JPS55149242A (it)
AT (1)	AT373235B (it)
CA (1)	CA1159834A (it)
CH (2)	CH646948A5 (it)
CY (2)	CY1316A (it)
DE (1)	DE3016110A1 (it)
ES (1)	ES8105259A1 (it)
FR (1)	FR2455034A1 (it)
GB (2)	GB2053195B (it)
HK (2)	HK1486A (it)
IT (1)	IT1188929B (it)
MY (2)	MY8600498A (it)
NL (1)	NL8002483A (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050058673A1 (en) *	2003-09-09	2005-03-17	3M Innovative Properties Company	Antimicrobial compositions and methods
BRPI0608691A2 (pt)	2005-03-10	2010-12-07	3M Innovative Properties Company	composição antimicrobiana, e, métodos para matar ou inativar microorganismos em tecido da mucosa de um mamìfero, para tratar uma lesão ou ferimento infectado, para descolonização de microorganismos, para proporcionar eficácia antimicrobiana residual sobre uma superfìcie e para tratar uma condição
WO2006099325A2 (en)	2005-03-10	2006-09-21	3M Innovative Properties Company	Methods of treating ear infections
EP1858482B1 (en)	2005-03-10	2014-04-23	3M Innovative Properties Company	Methods of reducing microbial contamination
WO2011061272A2 (en) *	2009-11-18	2011-05-26	Medichem S.A.	A di(4-chloro-phenyldiguanido) derivative which is free of potential genotoxicity and a process for reducing the residual amount of p-chloroaniline in said di(4-chloro-phenyldiguanido) derivative

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB815800A (en) *	1956-06-06	1959-07-01	Ici Ltd	New biguanide salts
US2684924A (en) *	1951-02-05	1954-07-27	Ici Ltd	Nu-chlorophenyldiguanidino compounds
US2990425A (en) *	1956-06-06	1961-06-27	Ici Ltd	New biguanide salts
US3159537A (en) *	1960-12-20	1964-12-01	American Cyanamid Co	Potentiation of tetracycline by phosphinic acid
BE612641A (it) *	1961-01-18
US3694447A (en) *	1970-03-10	1972-09-26	Smith Kline French Lab	Complexes of phosphanilic acid and 9-amino-3-nitroacridine
US3794723A (en) *	1970-03-10	1974-02-26	Smithkline Corp	Complexes of phosphanilic acid and 9-amino-3-nitroacridine useful as antifungal or antibacterial agents
SE370003B (it) *	1971-05-18	1974-09-30	Kema Nord Ab
GB1338003A (en) *	1971-06-18	1973-11-21	Ici Ltd	Cleaning compositions
SE374658B (it) *	1972-07-31	1975-03-17	Hesselgren S G
US3976765A (en) *	1973-11-01	1976-08-24	Colgate-Palmolive Company	Antibacterial oral preparations
US4125610A (en) *	1977-07-27	1978-11-14	Bristol-Myers Company	Antibacterial compositions

1980
- 1980-04-23 CA CA000350482A patent/CA1159834A/en not_active Expired
- 1980-04-24 IT IT48512/80A patent/IT1188929B/it active
- 1980-04-25 JP JP5439280A patent/JPS55149242A/ja active Pending
- 1980-04-25 GB GB8013786A patent/GB2053195B/en not_active Expired
- 1980-04-25 CH CH322480A patent/CH646948A5/de not_active IP Right Cessation
- 1980-04-25 CY CY1316A patent/CY1316A/en unknown
- 1980-04-25 FR FR8009398A patent/FR2455034A1/fr active Granted
- 1980-04-25 CH CH3086/84A patent/CH648755A5/de not_active IP Right Cessation
- 1980-04-25 DE DE19803016110 patent/DE3016110A1/de active Granted
- 1980-04-25 ES ES490947A patent/ES8105259A1/es not_active Expired
- 1980-04-25 CY CY1324A patent/CY1324A/en unknown
- 1980-04-28 NL NL8002483A patent/NL8002483A/nl not_active Application Discontinuation
- 1980-04-28 AT AT0227880A patent/AT373235B/de not_active IP Right Cessation
1982
- 1982-10-13 GB GB08229195A patent/GB2118041B/en not_active Expired
1986
- 1986-01-09 HK HK14/86A patent/HK1486A/xx unknown
- 1986-03-27 HK HK212/86A patent/HK21286A/xx unknown
- 1986-12-30 MY MY498/86A patent/MY8600498A/xx unknown
- 1986-12-30 MY MY495/86A patent/MY8600495A/xx unknown

Also Published As

Publication number	Publication date
NL8002483A (nl)	1980-10-28
CY1324A (en)	1986-06-27
FR2455034B1 (it)	1984-08-10
CH648755A5 (de)	1985-04-15
JPS55149242A (en)	1980-11-20
IT8048512A0 (it)	1980-04-24
DE3016110C2 (it)	1990-12-13
GB2118041B (en)	1984-03-21
CA1159834A (en)	1984-01-03
AT373235B (de)	1983-12-27
HK21286A (en)	1986-04-04
GB2118041A (en)	1983-10-26
HK1486A (en)	1986-01-17
FR2455034A1 (fr)	1980-11-21
GB2053195A (en)	1981-02-04
IT1188929B (it)	1988-01-28
DE3016110A1 (de)	1980-11-06
IT8048512A1 (it)	1981-10-24
ATA227880A (de)	1983-05-15
MY8600498A (en)	1986-12-31
MY8600495A (en)	1986-12-31
ES490947A0 (es)	1981-05-16
GB2053195B (en)	1983-04-07
CY1316A (en)	1986-03-28
ES8105259A1 (es)	1981-05-16

Legal Events

Date	Code	Title	Description
1996-12-13	PL	Patent ceased

Publication	Publication Date	Title
DE2708331C2 (it)	1991-03-21
US4666896A (en)	1987-05-19	Chlorhexidine salts and compositions of same
DE69322087T2 (de)	1999-04-08	Neues kristall von heterozyclischen bis(phosphonsäure) monohydrat-derivat
DE3205655C2 (it)	1988-12-08
EP0711774B1 (de)	2002-02-13	Neue kristalline Cephem-Säureadditionssalze und Verfahren zu ihrer Herstellung
DE2739661A1 (de)	1978-08-10	Jodderivat von benzalkoniumchlorid, verfahren zu seiner herstellung und diese verbindungen enthaltende arzneimittel
DE2641388C3 (de)	1981-02-05	3',4'-Didesoxykanamycin B-N-methansulfonsäuren und deren Alkalimetallsalze sowie diese Verbindungen enthaltende pharmazeutische Präparate
CH646948A5 (de)	1984-12-28	Chlorhexidinsalze und praeparate enthaltend dieselben.
DE2101378A1 (de)	1971-07-22	Neue pharmazeutische Zusammensetzungen zur Behandlung von Bakterieninfektionen
DE3133215C2 (de)	1983-10-27	N-Methansulfonsäurederivate von Istamycin A oder B, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2517600A1 (de)	1975-12-18	Neue gentamicinderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel
DE2655130C3 (de)	1982-05-06	Eine praktisch lösungsmittelfreie Kristallform des Cefacetril-Natriumsalzes
DE69705405T2 (de)	2001-11-08	Neue formen der organischen salze des n'n-diacetylcystins
DE2629599A1 (de)	1977-06-02	Beta-sulfenylacrylsaeure-verbindungen und verfahren zu ihrer herstellung
DE3236191C2 (de)	1986-06-05	Chlorhexidin-Dinaproxenat, Verfahren zu dessen Herstellung, sowie dieses enthaltende anti-entzündliche, desinfizierende und anti-bakterielle Zusammensetzung
DE1770889A1 (de)	1972-01-13	Wasserloesliche Mischungen von Sulfonamid- und Tetracyclin-Saeuresalzen
CA1148863A (en)	1983-06-28	Chlorhexidine salts and compositions of same
AT323745B (de)	1975-07-25	Verfahren zur herstellung von neuen 2,4-diamino-5-benzylpyrimidinen bzw. deren salzen
DE2156806C2 (de)	1983-04-28	Argininacetylsalicylate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE2154027C3 (de)	1977-02-03	alpha- (N-2-Pyrimidylf ormamidlno) benzylpenicillin sowie dessen nichttoxische Salze, Verfahren zu seiner Herstellung sowie es enthaltende Arzneimittel
CA1166155A (en)	1984-04-24	Method for inhibiting the growth of a microorganism on an inanimate substrate
DE1593015C3 (de)	1978-08-31	N.N'-Dimethyl-NJ'i'-di-detracyclinomethyl)-äthylendiamin und dessen Salze mit pharmakologisch unbedenklichen Mineral- und organischen Säuren sowie Verfahren zu deren Herstellung
DE3149478A1 (de)	1982-11-04	Imidazol-derivate
AT318807B (de)	1974-11-25	Verfahren zur Herstellung eines neuen Salzes eines Penicillinesters
DE2656783A1 (de)	1978-06-29	Verfahren zur herstellung von neuen chinoxalin-di-n-oxiden sowie ihre verwendung als arzneimittel