CA1070316A - Pharmacologically active bis imidazolyl guanidines - Google Patents
Pharmacologically active bis imidazolyl guanidinesInfo
- Publication number
- CA1070316A CA1070316A CA263,718A CA263718A CA1070316A CA 1070316 A CA1070316 A CA 1070316A CA 263718 A CA263718 A CA 263718A CA 1070316 A CA1070316 A CA 1070316A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- imidazolyl
- methylthio
- formula
- ethyl
- Prior art date
- 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
Links
- JBARCTHFPUHCED-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)guanidine Chemical class NC(=N)NC1=NC=CN1 JBARCTHFPUHCED-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- -1 2-[4-methyl-5-imidazolyl methylthio]-propyl Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- NPPYCTSQYCMZIB-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CSC(N)=[NH+]CCSCC=1N=CNC=1C.CSC(N)=[NH+]CCSCC=1N=CNC=1C NPPYCTSQYCMZIB-UHFFFAOYSA-N 0.000 claims description 2
- WZTVUNBRCHHEGT-UHFFFAOYSA-N 1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]guanidine Chemical compound N1C=NC(C)=C1CSC(C)CNC(=N)NCCSCC=1NC=NC=1C WZTVUNBRCHHEGT-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000005864 Sulphur Substances 0.000 abstract description 6
- 230000031018 biological processes and functions Effects 0.000 abstract description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 3
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 abstract description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical group BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 abstract description 2
- 210000000748 cardiovascular system Anatomy 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract description 2
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- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 32
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229960001340 histamine Drugs 0.000 description 16
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 15
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 14
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
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- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
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- 206010030113 Oedema Diseases 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical compound OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- OPGQGYQPVOWUOO-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NCCSCC=1N=CNC=1C OPGQGYQPVOWUOO-UHFFFAOYSA-N 0.000 description 1
- WSUNDBVVUCLXTG-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCSCC=1NC=NC=1C WSUNDBVVUCLXTG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MCWKMMXOIRBRQD-UHFFFAOYSA-N n-(dichloromethylidene)benzamide Chemical compound ClC(Cl)=NC(=O)C1=CC=CC=C1 MCWKMMXOIRBRQD-UHFFFAOYSA-N 0.000 description 1
- MVCKONDSKZNVRK-UHFFFAOYSA-N n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-1-methylsulfanyl-2-nitroethenamine Chemical group [O-][N+](=O)C=C(SC)NCCSCC=1NC=NC=1C MVCKONDSKZNVRK-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 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
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VJAMCQFRFWRULO-UHFFFAOYSA-N thiourea;dihydrochloride Chemical compound Cl.Cl.NC(S)=N VJAMCQFRFWRULO-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46732/75A GB1573611A (en) | 1975-11-12 | 1975-11-12 | Heterocyclic thioalkyl-amines-guanidines and -thioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070316A true CA1070316A (en) | 1980-01-22 |
Family
ID=10442384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,718A Expired CA1070316A (en) | 1975-11-12 | 1976-10-19 | Pharmacologically active bis imidazolyl guanidines |
Country Status (22)
-
1975
- 1975-11-12 GB GB46732/75A patent/GB1573611A/en not_active Expired
-
1976
- 1976-10-12 NZ NZ182309A patent/NZ182309A/xx unknown
- 1976-10-14 SE SE7611405A patent/SE7611405L/xx unknown
- 1976-10-18 ZA ZA766201A patent/ZA766201B/xx unknown
- 1976-10-19 CA CA263,718A patent/CA1070316A/en not_active Expired
- 1976-10-20 NL NL7611590A patent/NL7611590A/xx not_active Application Discontinuation
- 1976-10-21 AU AU18900/76A patent/AU508143B2/en not_active Expired
- 1976-10-22 IL IL50748A patent/IL50748A0/xx unknown
- 1976-10-26 IE IE2363/76A patent/IE44103B1/en unknown
- 1976-10-26 PT PT65759A patent/PT65759B/pt unknown
- 1976-10-29 DE DE19762649546 patent/DE2649546A1/de not_active Withdrawn
- 1976-11-04 AT AT819776A patent/AT350583B/de active
- 1976-11-08 DK DK503176A patent/DK503176A/da not_active Application Discontinuation
- 1976-11-08 BE BE172167A patent/BE848108A/xx not_active IP Right Cessation
- 1976-11-09 FI FI763209A patent/FI763209A7/fi not_active Application Discontinuation
- 1976-11-09 NO NO763812A patent/NO763812L/no unknown
- 1976-11-10 FR FR7633962A patent/FR2331342A1/fr active Granted
- 1976-11-10 JP JP51135826A patent/JPS5262274A/ja active Pending
- 1976-11-10 LU LU76162A patent/LU76162A1/xx unknown
- 1976-11-11 SU SU762418884A patent/SU634668A3/ru active
- 1976-11-11 HU HU76SI1548A patent/HU175667B/hu unknown
- 1976-11-12 ES ES453263A patent/ES453263A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE44103B1 (en) | 1981-08-12 |
| ZA766201B (en) | 1977-09-28 |
| DE2649546A1 (de) | 1977-05-26 |
| PT65759B (en) | 1978-04-27 |
| AU1890076A (en) | 1978-04-27 |
| SU634668A3 (ru) | 1978-11-25 |
| NO763812L (enrdf_load_stackoverflow) | 1977-05-13 |
| PT65759A (en) | 1976-11-01 |
| SE7611405L (sv) | 1977-05-13 |
| BE848108A (fr) | 1977-05-09 |
| NL7611590A (nl) | 1977-05-16 |
| AT350583B (de) | 1979-06-11 |
| ES453263A1 (es) | 1978-01-16 |
| FR2331342B1 (enrdf_load_stackoverflow) | 1980-03-07 |
| NZ182309A (en) | 1978-07-10 |
| JPS5262274A (en) | 1977-05-23 |
| IE44103L (en) | 1977-05-12 |
| GB1573611A (en) | 1980-08-28 |
| LU76162A1 (enrdf_load_stackoverflow) | 1977-05-18 |
| AU508143B2 (en) | 1980-03-13 |
| FI763209A7 (enrdf_load_stackoverflow) | 1977-05-13 |
| DK503176A (da) | 1977-05-13 |
| IL50748A0 (en) | 1976-12-31 |
| HU175667B (hu) | 1980-09-28 |
| ATA819776A (de) | 1978-11-15 |
| FR2331342A1 (fr) | 1977-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |