CA1081711A - 1-phenylguanidines - Google Patents

1-phenylguanidines

Info

Publication number: CA1081711A
Authority: CA; Canada
Prior art keywords: hydrogen; guanidine; chloro; methyl; loweralkyl
Prior art date: 1975-07-11
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

CA231,437A

Other languages

English (en)

Other versions

CA231437S (en

Inventor

Julius Diamond

George H. Douglas

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.)

William H Rorer Inc

Original Assignee

William H Rorer 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.)

1975-07-11

Filing date

1975-07-11

Publication date

1980-07-15

1975-07-11 Application filed by William H Rorer Inc filed Critical William H Rorer Inc

1975-07-11 Priority to CA231,437A priority Critical patent/CA1081711A/fr

1980-07-15 Application granted granted Critical

1980-07-15 Publication of CA1081711A publication Critical patent/CA1081711A/fr

Status Expired legal-status Critical Current

Links

QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 title description 6
239000001257 hydrogen Substances 0.000 claims abstract description 43
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
150000002431 hydrogen Chemical class 0.000 claims abstract description 15
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
-1 guanidine compound Chemical class 0.000 claims description 70
238000000034 method Methods 0.000 claims description 36
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 22
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 16
230000008569 process Effects 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 11
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 11
231100000252 nontoxic Toxicity 0.000 claims description 7
230000003000 nontoxic effect Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 5
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
229930003836 cresol Natural products 0.000 claims description 2
125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 7
RYEVBHAQZMEFTL-UHFFFAOYSA-N 2-(2,6-difluorophenyl)guanidine Chemical compound NC(=N)NC1=C(F)C=CC=C1F RYEVBHAQZMEFTL-UHFFFAOYSA-N 0.000 claims 2
SGBSVLLMNHLNAP-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)guanidine Chemical compound CC1=CC=CC(C)=C1NC(N)=N SGBSVLLMNHLNAP-UHFFFAOYSA-N 0.000 claims 2
NUSHYVKAWHLGOZ-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)guanidine Chemical compound NC(=N)NC1=C(F)C=CC=C1Cl NUSHYVKAWHLGOZ-UHFFFAOYSA-N 0.000 claims 2
VDWVNAHGRWQHMZ-UHFFFAOYSA-N 2-(2-chloro-6-methylphenyl)guanidine Chemical compound CC1=CC=CC(Cl)=C1NC(N)=N VDWVNAHGRWQHMZ-UHFFFAOYSA-N 0.000 claims 2
ZZAKSKPMOQLLQH-UHFFFAOYSA-N 2-(2-ethyl-6-methylphenyl)guanidine Chemical compound CCC1=CC=CC(C)=C1N=C(N)N ZZAKSKPMOQLLQH-UHFFFAOYSA-N 0.000 claims 2
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 20
230000000694 effects Effects 0.000 abstract description 7
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
230000000875 corresponding effect Effects 0.000 description 15
239000000047 product Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
229940083608 sodium hydroxide Drugs 0.000 description 11
235000011121 sodium hydroxide Nutrition 0.000 description 11
150000001412 amines Chemical class 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
150000001448 anilines Chemical class 0.000 description 8
238000009833 condensation Methods 0.000 description 8
230000005494 condensation Effects 0.000 description 8
229960004198 guanidine Drugs 0.000 description 8
150000002357 guanidines Chemical class 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
229940030600 antihypertensive agent Drugs 0.000 description 6
239000002220 antihypertensive agent Substances 0.000 description 6
239000012458 free base Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
WJKBLNUGJOFWDL-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-methylguanidine;hydrochloride Chemical compound Cl.CNC(=N)NC1=C(Cl)C=CC=C1Cl WJKBLNUGJOFWDL-UHFFFAOYSA-N 0.000 description 4
JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 4
FBVLZVUGJGEIEC-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)guanidine Chemical compound NC(=N)NC1=C(Cl)C=CC=C1Cl FBVLZVUGJGEIEC-UHFFFAOYSA-N 0.000 description 4
ZSJNJAJDBNFVCA-UHFFFAOYSA-N 2-(4-chlorophenyl)guanidine Chemical compound NC(=N)NC1=CC=C(Cl)C=C1 ZSJNJAJDBNFVCA-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
150000001912 cyanamides Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011369 resultant mixture Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
KUQHRGMPBWZVQR-UHFFFAOYSA-N (2,6-dichlorophenyl)thiourea Chemical compound NC(=S)NC1=C(Cl)C=CC=C1Cl KUQHRGMPBWZVQR-UHFFFAOYSA-N 0.000 description 2
HWDOZTDEGYETEM-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-1-methylguanidine Chemical compound NC(=N)N(C)C1=C(Cl)C=CC=C1Cl HWDOZTDEGYETEM-UHFFFAOYSA-N 0.000 description 2
DWLMIHRZURMFAQ-UHFFFAOYSA-N 2-(3-chlorophenyl)guanidine Chemical compound NC(N)=NC1=CC=CC(Cl)=C1 DWLMIHRZURMFAQ-UHFFFAOYSA-N 0.000 description 2
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical class NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229960001413 acetanilide Drugs 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
QISMFBCNJHJJJB-UHFFFAOYSA-N n-[amino-(2,6-dichloroanilino)methylidene]acetamide Chemical compound CC(=O)NC(=N)NC1=C(Cl)C=CC=C1Cl QISMFBCNJHJJJB-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
KHVNBZZFGKCREB-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-1-methylguanidine;hydrochloride Chemical compound Cl.NC(=N)N(C)C1=C(Cl)C=CC=C1Cl KHVNBZZFGKCREB-UHFFFAOYSA-N 0.000 description 1
GBKSZLKKOXQUAT-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-ethylguanidine Chemical compound CCNC(=N)NC1=C(Cl)C=CC=C1Cl GBKSZLKKOXQUAT-UHFFFAOYSA-N 0.000 description 1
XIBFIOFSBLXRDI-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-methylguanidine Chemical compound CNC(=N)NC1=C(Cl)C=CC=C1Cl XIBFIOFSBLXRDI-UHFFFAOYSA-N 0.000 description 1
CSWBIXLHZJCSSG-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC=C(F)C=C1 CSWBIXLHZJCSSG-UHFFFAOYSA-N 0.000 description 1
YEZHGQZHWKJPCM-UHFFFAOYSA-N 1-isothiocyanatooctane Chemical compound CCCCCCCCN=C=S YEZHGQZHWKJPCM-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
MNRQXYFZAROREY-UHFFFAOYSA-N 2,3-dibromoaniline Chemical compound NC1=CC=CC(Br)=C1Br MNRQXYFZAROREY-UHFFFAOYSA-N 0.000 description 1
FRJFKKCYRHRKRP-UHFFFAOYSA-N 2,6-dichloro-n-methylaniline Chemical compound CNC1=C(Cl)C=CC=C1Cl FRJFKKCYRHRKRP-UHFFFAOYSA-N 0.000 description 1
NSBSVUUVECHDDX-UHFFFAOYSA-N 2,6-dimethyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1N NSBSVUUVECHDDX-UHFFFAOYSA-N 0.000 description 1
XEMZMCKRNUQBIJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC1=C(Cl)C=CC=C1Cl XEMZMCKRNUQBIJ-UHFFFAOYSA-N 0.000 description 1
PXNBOFBSFXZTES-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)guanidine Chemical compound NC(=N)NC1=CC(Cl)=CC(Cl)=C1 PXNBOFBSFXZTES-UHFFFAOYSA-N 0.000 description 1
RMFZXBDENVVLSL-UHFFFAOYSA-N 2-(4-chlorophenyl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC1=CC=C(Cl)C=C1 RMFZXBDENVVLSL-UHFFFAOYSA-N 0.000 description 1
ZLYDHHZPLXBVQW-UHFFFAOYSA-N 2-(4-fluorophenyl)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC1=CC=C(F)C=C1 ZLYDHHZPLXBVQW-UHFFFAOYSA-N 0.000 description 1
JHHMLFBYFNAPDZ-UHFFFAOYSA-N 2-bromo-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1Br JHHMLFBYFNAPDZ-UHFFFAOYSA-N 0.000 description 1
SKWDIXBVQATQSG-UHFFFAOYSA-N 2-chloro-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(O)=O)=C1 SKWDIXBVQATQSG-UHFFFAOYSA-N 0.000 description 1
YTXHOVZVLJTSLH-UHFFFAOYSA-N 2-methylazocane piperazine Chemical compound CC1NCCCCCC1.N1CCNCC1 YTXHOVZVLJTSLH-UHFFFAOYSA-N 0.000 description 1
VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
LBYVZRFDLNAPRC-UHFFFAOYSA-N 2-sulfanylguanidine Chemical compound NC(=N)NS LBYVZRFDLNAPRC-UHFFFAOYSA-N 0.000 description 1
QFTJOYLPELHHCO-UHFFFAOYSA-N 3,4-dibromoaniline Chemical compound NC1=CC=C(Br)C(Br)=C1 QFTJOYLPELHHCO-UHFFFAOYSA-N 0.000 description 1
FVZODFVCIDBDGS-UHFFFAOYSA-N 3-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C(Br)=C1 FVZODFVCIDBDGS-UHFFFAOYSA-N 0.000 description 1
BVVFDOMNUHCQSA-UHFFFAOYSA-N 3-bromoaniline 4-bromoaniline Chemical compound BrC1=CC=C(N)C=C1.BrC=1C=C(N)C=CC1 BVVFDOMNUHCQSA-UHFFFAOYSA-N 0.000 description 1
QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
SFCQVEDGNZVACI-UHFFFAOYSA-N 3-isothiocyanato-2-methylprop-1-ene Chemical compound CC(=C)CN=C=S SFCQVEDGNZVACI-UHFFFAOYSA-N 0.000 description 1
XCXOHPXTLZMKQJ-UHFFFAOYSA-N 3-isothiocyanatoprop-1-yne Chemical compound S=C=NCC#C XCXOHPXTLZMKQJ-UHFFFAOYSA-N 0.000 description 1
MPNDLCBMLBACDD-UHFFFAOYSA-N 4-fluoro-2,6-dimethylaniline Chemical compound CC1=CC(F)=CC(C)=C1N MPNDLCBMLBACDD-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
ZTQZWZJXCFTDGI-UHFFFAOYSA-N BrC1=C(N)C=C(C=C1)Br.BrC1=C(N)C=CC(=C1)Br Chemical compound BrC1=C(N)C=C(C=C1)Br.BrC1=C(N)C=CC(=C1)Br ZTQZWZJXCFTDGI-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
YYVROSOSINUJNF-UHFFFAOYSA-N C(C#C)N.C(CCCCCCC)N.C(CCCCCC)N.C(CCCCC)N.C(CCCC)N.C(CCC)N.C(C)(C)N.C(CC)N.C(C)N Chemical compound C(C#C)N.C(CCCCCCC)N.C(CCCCCC)N.C(CCCCC)N.C(CCCC)N.C(CCC)N.C(C)(C)N.C(CC)N.C(C)N YYVROSOSINUJNF-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
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239000008096 xylene Substances 0.000 description 1

Landscapes

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

CA231,437A 1975-07-11 1975-07-11 1-phenylguanidines Expired CA1081711A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA231,437A CA1081711A (fr)	1975-07-11	1975-07-11	1-phenylguanidines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA231,437A CA1081711A (fr)	1975-07-11	1975-07-11	1-phenylguanidines

Publications (1)

Publication Number	Publication Date
CA1081711A true CA1081711A (fr)	1980-07-15

Family

ID=4103606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA231,437A Expired CA1081711A (fr)	1975-07-11	1975-07-11	1-phenylguanidines

Country Status (1)

Country	Link
CA (1)	CA1081711A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6025355A (en)	1997-05-19	2000-02-15	Cambridge Neuroscience, Inc.	Pharmaceutically active compounds and methods of use
US6242198B1 (en)	1996-07-25	2001-06-05	Cambridge Neuroscience, Inc.	Methods of treatment of eye trauma and disorders
US6756389B2 (en)	1996-08-09	2004-06-29	Cambridge Neuroscience, Inc.	Pharmaceutically active compounds and methods of use

1975
- 1975-07-11 CA CA231,437A patent/CA1081711A/fr not_active Expired

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6358993B1 (en)	1996-02-15	2002-03-19	Cenes Pharmaceuticals, Inc.	Pharmaceutically active nitrogen ring compounds and methods of use thereof
US6514990B2 (en)	1996-02-15	2003-02-04	Scion Pharmaceuticals, Inc.	Pharmaceutically active compounds and methods of use
US6770668B2 (en)	1996-02-15	2004-08-03	N. Laxma Reddy	Pharmaceutically active compounds and methods of use
US6242198B1 (en)	1996-07-25	2001-06-05	Cambridge Neuroscience, Inc.	Methods of treatment of eye trauma and disorders
US6358696B1 (en)	1996-07-25	2002-03-19	Mcburney Robert N.	Methods of treatment of eye trauma and disorders
US6673557B2 (en)	1996-07-25	2004-01-06	Mcburney Robert N.	Methods of treatment of eye trauma and disorders
US6756389B2 (en)	1996-08-09	2004-06-29	Cambridge Neuroscience, Inc.	Pharmaceutically active compounds and methods of use
US7423059B2 (en)	1996-08-09	2008-09-09	Wyeth	Pharmaceutically active compounds and methods of use
US6025355A (en)	1997-05-19	2000-02-15	Cambridge Neuroscience, Inc.	Pharmaceutically active compounds and methods of use

Legal Events

Date	Code	Title	Description
1997-07-15	MKEX	Expiry

Publication	Publication Date	Title
US3976643A (en)	1976-08-24	Guanidines
US4025652A (en)	1977-05-24	Amidinoureas
US4060635A (en)	1977-11-29	Amidinoureas for treating diarrhea
US4326075A (en)	1982-04-20	Amidinoureas
US4326074A (en)	1982-04-20	Amidinoureas
LT4343B (lt)	1998-05-25	Anilino dariniai,pasižymintys inhibitoriniu veikimu azoto oksido sintazei
BRPI0614805A2 (pt)	2011-04-12	poliaminas úteis como produtos terapêuticos antiparasìticos e anticáncer e como inibidores de demetilase lisina-especìficos
US3168562A (en)	1965-02-02	Substituted benzylguanidines
CA2378456C (fr)	2012-04-10	Composes liant l'albumine qui empechent la glycation non enzymatique et qui peuvent etre utilises dans le traitement de pathologies liees a la glycation
US3914306A (en)	1975-10-21	Guanidines
US4088785A (en)	1978-05-09	Amidinoureas for the treatment of cardinascular disorders
CA1081711A (fr)	1980-07-15	1-phenylguanidines
US4117165A (en)	1978-09-26	Amidinoureas
US3996232A (en)	1976-12-07	1,5-Disubstituted biguanides
Cason et al.	1951	The Preparation of Some Aryl Aminoalkyl Sulfides and Sulfones1, 2
US4505929A (en)	1985-03-19	Sulfur-substituted diphenyl ethers having antiviral activity
CA1041908A (fr)	1978-11-07	Amidinourees
US4220658A (en)	1980-09-02	Treatment of hypertension with amidinoureas
CA1081709A (fr)	1980-07-15	Composes a base de phenylamidinouree
US4349568A (en)	1982-09-14	Sulfur-substituted diphenyl ethers having antiviral activity
ZENITZ et al.	1946	AMINO ALCOHOLS. XVI. 1 PHENYL HALOGENATED PROPADRINES
AU724616B2 (en)	2000-09-28	Process for the preparation of benzothiazolone compounds
US4488993A (en)	1984-12-18	Amidinoureas
US3928603A (en)	1975-12-23	New derivatives of alpha-methyl benzylamine in treating inflammation
BURGER et al.	1956	Chlorinated o-Dimethylaminopropylaminodiphenyl Sulfide Derivatives