CA1260938A - Pyrimidine-thioalkyl pyridine derivatives, a process for their production and medicaments containing these compounds - Google Patents
Pyrimidine-thioalkyl pyridine derivatives, a process for their production and medicaments containing these compoundsInfo
- Publication number
- CA1260938A CA1260938A CA000451173A CA451173A CA1260938A CA 1260938 A CA1260938 A CA 1260938A CA 000451173 A CA000451173 A CA 000451173A CA 451173 A CA451173 A CA 451173A CA 1260938 A CA1260938 A CA 1260938A
- Authority
- CA
- Canada
- Prior art keywords
- compound according
- pyrimidine
- compound
- amino
- hydrogen
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000003574 free electron Substances 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 9
- -1 sulfinyl compound Chemical class 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
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- 230000001225 therapeutic effect Effects 0.000 abstract description 3
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
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- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 2
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- 150000007944 thiolates Chemical class 0.000 description 2
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- 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
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 210000003097 mucus Anatomy 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP83104452.4 | 1983-05-05 | ||
| EP83104452A EP0124630B1 (de) | 1983-05-05 | 1983-05-05 | Pyrimidin-Thioalkylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1260938A true CA1260938A (en) | 1989-09-26 |
Family
ID=8190450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000451173A Expired CA1260938A (en) | 1983-05-05 | 1984-04-03 | Pyrimidine-thioalkyl pyridine derivatives, a process for their production and medicaments containing these compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5025016A (en, 2012) |
| EP (1) | EP0124630B1 (en, 2012) |
| JP (1) | JPS59210081A (en, 2012) |
| KR (1) | KR900005110B1 (en, 2012) |
| AT (1) | ATE25255T1 (en, 2012) |
| AU (1) | AU567556B2 (en, 2012) |
| CA (1) | CA1260938A (en, 2012) |
| DE (1) | DE3369514D1 (en, 2012) |
| DK (1) | DK160761C (en, 2012) |
| ES (2) | ES8604201A1 (en, 2012) |
| GR (1) | GR81592B (en, 2012) |
| HU (1) | HU192015B (en, 2012) |
| IE (1) | IE57330B1 (en, 2012) |
| IL (1) | IL71441A (en, 2012) |
| NZ (1) | NZ208056A (en, 2012) |
| PT (1) | PT78362B (en, 2012) |
| YU (2) | YU45081B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU203736B (en) * | 1989-04-06 | 1991-09-30 | Gyogyszerkutato Intezet | Process for producing new thiouracil-derivatives and pharmaceutical compositions containing them |
| US5981537A (en) * | 1993-11-12 | 1999-11-09 | Pharmacia & Upjohn Company | Pyrimidine-thioalkyl and alkylether compounds |
| UA56992C2 (uk) * | 1995-05-08 | 2003-06-16 | Фармація Енд Апджон Компані | <font face="Symbol">a</font>-ПІРИМІДИНТІОАЛКІЛЗАМІЩЕНІ ТА <font face="Symbol">a</font>-ПІРИМІДИНОКСОАЛКІЛЗАМІЩЕНІ СПОЛУКИ |
| CN1309656A (zh) * | 1997-09-25 | 2001-08-22 | 法玛西雅厄普约翰美国公司 | 烷硫基α－取代的嘧啶化合物 |
| US7358254B2 (en) * | 2001-07-13 | 2008-04-15 | Bristol-Myers Squibb Company | Method for treating atherosclerosis employing an aP2 inhibitor and combination |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1092343B (it) * | 1978-02-02 | 1985-07-06 | Poli Ind Chimica Spa | Pirimidilsolfuri ad attivita' antisecretoria,processo per la loro preparazione e composizioni farmaceutiche che li contengono |
| DE3216843C2 (de) * | 1982-05-05 | 1986-10-23 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | 3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
-
1983
- 1983-05-05 EP EP83104452A patent/EP0124630B1/de not_active Expired
- 1983-05-05 DE DE8383104452T patent/DE3369514D1/de not_active Expired
- 1983-05-05 AT AT83104452T patent/ATE25255T1/de not_active IP Right Cessation
-
1984
- 1984-02-28 DK DK117984A patent/DK160761C/da not_active IP Right Cessation
- 1984-03-30 ES ES531164A patent/ES8604201A1/es not_active Expired
- 1984-04-03 PT PT78362A patent/PT78362B/pt not_active IP Right Cessation
- 1984-04-03 CA CA000451173A patent/CA1260938A/en not_active Expired
- 1984-04-04 GR GR74314A patent/GR81592B/el unknown
- 1984-04-05 IL IL71441A patent/IL71441A/xx unknown
- 1984-04-19 AU AU27173/84A patent/AU567556B2/en not_active Ceased
- 1984-04-24 YU YU727/84A patent/YU45081B/xx unknown
- 1984-04-25 HU HU841594A patent/HU192015B/hu not_active IP Right Cessation
- 1984-04-30 IE IE1065/84A patent/IE57330B1/en not_active IP Right Cessation
- 1984-05-01 JP JP59089157A patent/JPS59210081A/ja active Granted
- 1984-05-01 KR KR1019840002350A patent/KR900005110B1/ko not_active Expired
- 1984-05-04 NZ NZ208056A patent/NZ208056A/en unknown
-
1985
- 1985-06-25 ES ES544542A patent/ES8603865A1/es not_active Expired
-
1986
- 1986-08-08 YU YU1414/86A patent/YU45354B/xx unknown
-
1988
- 1988-09-26 US US07/248,927 patent/US5025016A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
| US9315521B2 (en) | 2009-05-21 | 2016-04-19 | UNIVERSITé LAVAL | Pyrimidines as novel therapeutic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| KR840009100A (ko) | 1984-12-24 |
| IE841065L (en) | 1985-11-05 |
| DK160761C (da) | 1991-09-23 |
| ES544542A0 (es) | 1986-01-16 |
| JPS59210081A (ja) | 1984-11-28 |
| HU192015B (en) | 1987-04-28 |
| PT78362A (de) | 1984-05-01 |
| DK117984A (da) | 1984-11-06 |
| IE57330B1 (en) | 1992-07-29 |
| YU45354B (en) | 1992-05-28 |
| YU141486A (en) | 1988-02-29 |
| DE3369514D1 (en) | 1987-03-05 |
| DK160761B (da) | 1991-04-15 |
| AU2717384A (en) | 1984-11-08 |
| PT78362B (de) | 1986-05-28 |
| IL71441A0 (en) | 1984-07-31 |
| YU45081B (en) | 1992-03-10 |
| YU72784A (en) | 1986-12-31 |
| GR81592B (en, 2012) | 1984-12-11 |
| ES8603865A1 (es) | 1986-01-16 |
| KR900005110B1 (ko) | 1990-07-19 |
| ES8604201A1 (es) | 1986-02-01 |
| JPH0451554B2 (en, 2012) | 1992-08-19 |
| ATE25255T1 (de) | 1987-02-15 |
| AU567556B2 (en) | 1987-11-26 |
| EP0124630A1 (de) | 1984-11-14 |
| HUT34466A (en) | 1985-03-28 |
| DK117984D0 (da) | 1984-02-28 |
| EP0124630B1 (de) | 1987-01-28 |
| US5025016A (en) | 1991-06-18 |
| IL71441A (en) | 1987-02-27 |
| ES531164A0 (es) | 1986-02-01 |
| NZ208056A (en) | 1986-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20060926 |