CA1136128A - Substances antimicrobiennes a base de bis-carbamylguanidinoazaalcanes - Google Patents

Substances antimicrobiennes a base de bis-carbamylguanidinoazaalcanes

Info

Publication number: CA1136128A
Authority: CA; Canada
Prior art keywords: acid; alkyl; group; bis; formula
Prior art date: 1975-10-30
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

CA000264357A

Other languages

English (en)

Inventor

Julius Diamond

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.)

Cooper Laboratories Inc

Original Assignee

Cooper Laboratories Inc

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.)

1975-10-30

Filing date

1976-10-28

Publication date

1982-11-23

1976-10-25 Priority claimed from DE19762648858 external-priority patent/DE2648858A1/de

1976-10-28 Application filed by Cooper Laboratories Inc filed Critical Cooper Laboratories Inc

1982-11-23 Application granted granted Critical

1982-11-23 Publication of CA1136128A publication Critical patent/CA1136128A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 83
230000000845 anti-microbial effect Effects 0.000 title abstract description 21
-1 loweralkoxy Chemical group 0.000 claims abstract description 284
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
150000007524 organic acids Chemical class 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000004350 aryl cycloalkyl group Chemical group 0.000 claims abstract description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
125000001475 halogen functional group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 23
230000008569 process Effects 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000012948 isocyanate Substances 0.000 claims description 6
150000002513 isocyanates Chemical class 0.000 claims description 6
229940098779 methanesulfonic acid Drugs 0.000 claims description 6
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
125000005059 halophenyl group Chemical group 0.000 claims description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
239000000174 gluconic acid Substances 0.000 claims description 4
235000012208 gluconic acid Nutrition 0.000 claims description 4
150000002357 guanidines Chemical class 0.000 claims description 4
125000006277 halobenzyl group Chemical group 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 4
NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 claims description 3
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims description 3
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
125000006177 alkyl benzyl group Chemical group 0.000 claims description 3
235000015165 citric acid Nutrition 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
229940099563 lactobionic acid Drugs 0.000 claims description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
239000011976 maleic acid Substances 0.000 claims description 3
229910017604 nitric acid Inorganic materials 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
235000011087 fumaric acid Nutrition 0.000 claims description 2
229950006191 gluconic acid Drugs 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
239000001630 malic acid Substances 0.000 claims description 2
235000011090 malic acid Nutrition 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
PXBUCJAIKQYENV-UHFFFAOYSA-N 2-[3-[4-[3-(diaminomethylideneamino)propyl]piperazin-1-yl]propyl]guanidine Chemical compound NC(N)=NCCCN1CCN(CCCN=C(N)N)CC1 PXBUCJAIKQYENV-UHFFFAOYSA-N 0.000 claims 3
QTUYLERIKLLYEH-UHFFFAOYSA-N 1-carbamimidoyl-1-[3-[4-[3-[carbamimidoyl(hexylcarbamoyl)amino]propyl]piperazin-1-yl]propyl]-3-hexylurea Chemical compound CCCCCCNC(=O)N(C(N)=N)CCCN1CCN(CCCN(C(N)=N)C(=O)NCCCCCC)CC1 QTUYLERIKLLYEH-UHFFFAOYSA-N 0.000 claims 2
FDPTWYDILIGTLK-UHFFFAOYSA-N 1-carbamimidoyl-1-[3-[4-[3-[carbamimidoyl(hexylcarbamoyl)amino]propyl]piperazin-1-yl]propyl]-3-hexylurea;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CCCCCCNC(=O)N(C(N)=N)CCCN1CCN(CCCN(C(N)=N)C(=O)NCCCCCC)CC1 FDPTWYDILIGTLK-UHFFFAOYSA-N 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
235000010323 ascorbic acid Nutrition 0.000 claims 2
229960005070 ascorbic acid Drugs 0.000 claims 2
239000011668 ascorbic acid Substances 0.000 claims 2
GCUFEQPYIUTCSA-UHFFFAOYSA-N 1-carbamimidoyl-1-[3-[4-[3-[carbamimidoyl-[(4-chlorophenyl)carbamoyl]amino]propyl]piperazin-1-yl]propyl]-3-(4-chlorophenyl)urea Chemical compound C=1C=C(Cl)C=CC=1NC(=O)N(C(=N)N)CCCN(CC1)CCN1CCCN(C(N)=N)C(=O)NC1=CC=C(Cl)C=C1 GCUFEQPYIUTCSA-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
125000002993 cycloalkylene group Chemical group 0.000 claims 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 claims 1
229940098895 maleic acid Drugs 0.000 claims 1
125000005915 C6-C14 aryl group Chemical group 0.000 abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 abstract description 4
125000005592 polycycloalkyl group Polymers 0.000 abstract description 3
125000003282 alkyl amino group Chemical group 0.000 abstract description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 20
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
125000003277 amino group Chemical group 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
229920000768 polyamine Polymers 0.000 description 10
GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound 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 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
229960003260 chlorhexidine Drugs 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 8
210000000214 mouth Anatomy 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000004599 antimicrobial Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
230000000699 topical effect Effects 0.000 description 6
239000002609 medium Substances 0.000 description 5
244000005700 microbiome Species 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
235000019640 taste Nutrition 0.000 description 5
241000894006 Bacteria Species 0.000 description 4
229940123208 Biguanide Drugs 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000000477 aza group Chemical group 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
238000001802 infusion Methods 0.000 description 4
210000002200 mouth mucosa Anatomy 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000001302 tertiary amino group Chemical group 0.000 description 4
208000002064 Dental Plaque Diseases 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
150000004287 bisbiguanides Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
125000006622 cycloheptylmethyl group Chemical group 0.000 description 3
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229960005141 piperazine Drugs 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
230000014860 sensory perception of taste Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000012085 test solution Substances 0.000 description 3
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
241000194019 Streptococcus mutans Species 0.000 description 2
231100000460 acute oral toxicity Toxicity 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000004283 biguanides Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000002324 mouth wash Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000007505 plaque formation Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000013207 serial dilution Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
NSMXQKNUPPXBRG-SECBINFHSA-N (R)-lisofylline Chemical group O=C1N(CCCC[C@H](O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-SECBINFHSA-N 0.000 description 1
VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
AHHGPQZCXVTEML-UHFFFAOYSA-N 2-[3-[4-[3-(diaminomethylideneamino)propyl]piperazin-1-yl]propyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NCCCN1CCN(CCCN=C(N)N)CC1 AHHGPQZCXVTEML-UHFFFAOYSA-N 0.000 description 1
CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical class CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
241000237518 Arion Species 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
239000004135 Bone phosphate Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
238000006969 Curtius rearrangement reaction Methods 0.000 description 1
206010013911 Dysgeusia Diseases 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
229950010221 alexidine Drugs 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000002882 anti-plaque Effects 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
GIVGDJZVMHYWDM-UHFFFAOYSA-N cyanourea Chemical class NC(=O)NC#N GIVGDJZVMHYWDM-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
210000001315 dental pellicle Anatomy 0.000 description 1
125000004341 endo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
DWYMPOCYEZONEA-UHFFFAOYSA-N fluorophosphoric acid Chemical compound OP(O)(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
210000004283 incisor Anatomy 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
MROAQUNKLFXYQN-UHFFFAOYSA-N methanamine;sulfuric acid Chemical compound NC.OS(O)(=O)=O MROAQUNKLFXYQN-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
230000007269 microbial metabolism Effects 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
239000001974 tryptic soy broth Substances 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000264357A 1975-10-30 1976-10-28 Substances antimicrobiennes a base de bis-carbamylguanidinoazaalcanes Expired CA1136128A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US62713975A	1975-10-30	1975-10-30
DEP2648858.4		1976-10-25
DE19762648858 DE2648858A1 (de)	1975-10-30	1976-10-25	Antimikrobielle verbindungen auf der grundlage von bis-carbamylguanidinoazaalkanen
US05/735,319 US4110328A (en)	1975-10-30	1976-10-26	Bis-carbamylguanidinoazaalkane antimicrobial compounds
US735,319		1976-10-26
US627,139		1984-07-02

Publications (1)

Publication Number	Publication Date
CA1136128A true CA1136128A (fr)	1982-11-23

Family

ID=27187020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000264357A Expired CA1136128A (fr)	1975-10-30	1976-10-28	Substances antimicrobiennes a base de bis-carbamylguanidinoazaalcanes

Country Status (1)

Country	Link
CA (1)	CA1136128A (fr)

1976
- 1976-10-28 CA CA000264357A patent/CA1136128A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-11-23	MKEX	Expiry

Publication	Publication Date	Title
US4022834A (en)	1977-05-10	Antibacterially active hexamethylene-bis-biguanides
US4115447A (en)	1978-09-19	Carbamylguanidine antimicrobial compounds
CH616667A5 (fr)	1980-04-15
BG104853A (en)	2001-04-30	Thienylazolylalcoxyethanamines, their preparation and their application as medicaments
DE69019293T2 (de)	1995-09-07	Naphthyloxazolidon-Derivate.
CA1237129A (fr)	1988-05-24	Derives d'aminoguanidine, et leur preparation
US4110328A (en)	1978-08-29	Bis-carbamylguanidinoazaalkane antimicrobial compounds
AU668709B2 (en)	1996-05-16	N,N'-substituted imidocarbonimidic diamides derived from hydroxylamines
ATE102482T1 (de)	1994-03-15	Verwendung von 1,4-disubstituierten-piperidinyl- verbindungen zur herstellung eines arzneimittels zur behandlung von schlaflosigkeit.
DE69903040T2 (de)	2003-06-26	Piperazinderivate zur replikationshemmung von menschlichem immundefizienz virus
CA1136128A (fr)	1982-11-23	Substances antimicrobiennes a base de bis-carbamylguanidinoazaalcanes
HU184871B (en)	1984-10-29	Process for preparing taurine derivatives
DE1545714A1 (de)	1969-06-26	Neue N-Aralkyl-piperidyl-1,3-dioxolane und Verfahren zur Herstellung derselben
HU199817B (en)	1990-03-28	Process for production of new derivatives of alkylendiamin and medical compositions containing them
US4166827A (en)	1979-09-04	Bis-carbamylguanidinoazaalkane antimicrobial compounds
EP0187700A1 (fr)	1986-07-16	Nouveaux dérivés de l'urée substitués par un groupe aminoalkyle, leurs sels d'addition acides et énantiomères
US4163022A (en)	1979-07-31	Carbamylguanidine antimicrobial compounds
DE1302662B (fr)	1971-02-04
GB1567463A (en)	1980-05-14	Bis-carbamylguanidinozaalkane antimicrobial compounds
US3255207A (en)	1966-06-07	Quaternary ammonium salts containing anilido groups
DE1695790C3 (de)	1974-07-04	S-Phenoxythionocarbonylderivate des Vitamins B tief 1
DE69405816T2 (de)	1998-01-15	Allophansäure Derivate
DE1939738A1 (de)	1971-02-18	Aminoguanidine und Verfahren zur Herstellung derselben
DE1670907B2 (de)	1976-07-22	N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung
DD298915A5 (de)	1992-03-19	Verfahren zur herstellung von pharmakologisch wirksamen 3-aminopyrrolen