NO119838B - - Google Patents
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- Publication number
- NO119838B NO119838B NO16110265A NO16110265A NO119838B NO 119838 B NO119838 B NO 119838B NO 16110265 A NO16110265 A NO 16110265A NO 16110265 A NO16110265 A NO 16110265A NO 119838 B NO119838 B NO 119838B
- Authority
- NO
- Norway
- Prior art keywords
- pyrimidine
- triamino
- phenylpyrido
- methyl
- diamino
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 claims description 2
- -1 2,4,7-triamino-6-benzyl-5-methylpyrido(2,3-d)pyrimidine Chemical compound 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IVNRMOHZVFDAJT-UHFFFAOYSA-N 6-methyl-5-phenylpyrido[2,3-d]pyrimidine-2,4,7-triamine Chemical compound NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)C)N)N IVNRMOHZVFDAJT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 description 1
- LWRSISCBGIMEQP-UHFFFAOYSA-N 2,4-diamino-6-methyl-5-phenyl-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)C)O)N LWRSISCBGIMEQP-UHFFFAOYSA-N 0.000 description 1
- RJJLZYAUABPVCK-UHFFFAOYSA-N 6-benzyl-7-chloro-5-methylpyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound ClC1=NC2=NC(N)=NC(N)=C2C(C)=C1CC1=CC=CC=C1 RJJLZYAUABPVCK-UHFFFAOYSA-N 0.000 description 1
- VVJHWKHRQBSXQO-UHFFFAOYSA-N 6-methyl-5-phenylpyrido[2,3-d]pyrimidine-2,4,7-triamine hydrate hydrochloride Chemical compound O.Cl.NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)C)N)N VVJHWKHRQBSXQO-UHFFFAOYSA-N 0.000 description 1
- ZVJGHESZYZVOKS-UHFFFAOYSA-N 7-chloro-5-phenylpyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound NC=1N=C(C2=C(N1)N=C(C=C2C2=CC=CC=C2)Cl)N ZVJGHESZYZVOKS-UHFFFAOYSA-N 0.000 description 1
- RLNRCDCMELQWDT-UHFFFAOYSA-N 7-chloro-6-methyl-5-phenylpyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)C)Cl)N RLNRCDCMELQWDT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 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 1
- IYQAEUJLSQIRRM-UHFFFAOYSA-N O.Cl.NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)CC)N)N Chemical compound O.Cl.NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)CC)N)N IYQAEUJLSQIRRM-UHFFFAOYSA-N 0.000 description 1
- UHAPUGJJEIMEOO-UHFFFAOYSA-N O.Cl.NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)CCC)N)N Chemical compound O.Cl.NC=1N=C(C2=C(N1)N=C(C(=C2C2=CC=CC=C2)CCC)N)N UHAPUGJJEIMEOO-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-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
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical class N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 229940097271 other diuretics in atc Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LDPNALMMCVBWGW-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine-2,4,7-triamine Chemical class NC1=NC(N)=NC2=NC(N)=CC=C21 LDPNALMMCVBWGW-UHFFFAOYSA-N 0.000 description 1
- LYXZTYXDCZQKSS-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine-2,4-diamine Chemical class C1=CC=NC2=NC(N)=NC(N)=C21 LYXZTYXDCZQKSS-UHFFFAOYSA-N 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000002700 urine Anatomy 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA920309 | 1965-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119838B true NO119838B (pl) | 1970-07-13 |
Family
ID=4142159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16110265A NO119838B (pl) | 1965-01-07 | 1965-12-31 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT260261B (pl) |
| BE (1) | BE674392A (pl) |
| BR (1) | BR6676280D0 (pl) |
| DE (1) | DE1620721A1 (pl) |
| DK (1) | DK116444B (pl) |
| ES (1) | ES321477A1 (pl) |
| FR (2) | FR1482853A (pl) |
| LU (1) | LU50189A1 (pl) |
| MC (1) | MC585A1 (pl) |
| NL (1) | NL6600213A (pl) |
| NO (1) | NO119838B (pl) |
-
1965
- 1965-12-27 DE DE19651620721 patent/DE1620721A1/de active Pending
- 1965-12-28 BE BE674392A patent/BE674392A/xx unknown
- 1965-12-31 NO NO16110265A patent/NO119838B/no unknown
-
1966
- 1966-01-03 LU LU50189D patent/LU50189A1/xx unknown
- 1966-01-04 AT AT5566A patent/AT260261B/de active
- 1966-01-05 ES ES0321477A patent/ES321477A1/es not_active Expired
- 1966-01-06 MC MC603A patent/MC585A1/xx unknown
- 1966-01-06 FR FR45046A patent/FR1482853A/fr not_active Expired
- 1966-01-06 DK DK7566A patent/DK116444B/da unknown
- 1966-01-07 NL NL6600213A patent/NL6600213A/xx unknown
- 1966-01-07 BR BR17628066A patent/BR6676280D0/pt unknown
- 1966-04-05 FR FR56481A patent/FR5433M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE674392A (pl) | 1966-06-28 |
| FR5433M (pl) | 1967-11-13 |
| LU50189A1 (pl) | 1966-07-04 |
| NL6600213A (pl) | 1966-07-08 |
| DE1620721A1 (de) | 1969-12-11 |
| BR6676280D0 (pt) | 1973-09-06 |
| DK116444B (da) | 1970-01-12 |
| MC585A1 (fr) | 1966-11-02 |
| FR1482853A (fr) | 1967-09-21 |
| AT260261B (de) | 1968-02-26 |
| ES321477A1 (es) | 1967-02-01 |
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