CA1137084A - 7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8 - Google Patents

7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8

Info

Publication number: CA1137084A
Authority: CA; Canada
Prior art keywords: carbon atoms; formula; hydrogen; compound; phenyl
Prior art date: 1979-08-08
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

CA000357364A

Other languages

English (en)

Inventor

Hans A. Wagner

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.)

GD Searle LLC

Original Assignee

GD Searle LLC

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.)

1979-08-08

Filing date

1980-07-30

Publication date

1982-12-07

1980-07-30 Application filed by GD Searle LLC filed Critical GD Searle LLC

1980-07-30 Priority to CA000357364A priority Critical patent/CA1137084A/fr

1982-12-07 Application granted granted Critical

1982-12-07 Publication of CA1137084A publication Critical patent/CA1137084A/fr

Status Expired legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 13
238000000034 method Methods 0.000 claims description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
-1 2-ethoxyethyl Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims 4
IJCSVLJXGQZUEU-UHFFFAOYSA-N 8-(2-ethoxyethyl)-7-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound N1=C(N)N2C=NN=C2C(CCOCC)=C1C1=CC=CC=C1 IJCSVLJXGQZUEU-UHFFFAOYSA-N 0.000 claims 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
FIPBRZXDWSODDX-UHFFFAOYSA-N 4-chloro-6-phenylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C=2C=CC=CC=2)=N1 FIPBRZXDWSODDX-UHFFFAOYSA-N 0.000 claims 1
FWNFVGBOBJFHHJ-UHFFFAOYSA-N 8-methyl-7-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound N1=C(N)N2C=NN=C2C(C)=C1C1=CC=CC=C1 FWNFVGBOBJFHHJ-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims 1
VJOCYFUVZJLYJM-UHFFFAOYSA-N n-(8-methyl-7-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)acetamide Chemical compound CC=1C2=NN=CN2C(NC(=O)C)=NC=1C1=CC=CC=C1 VJOCYFUVZJLYJM-UHFFFAOYSA-N 0.000 claims 1
239000002934 diuretic Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
JXXFPVBMCMWXBN-UHFFFAOYSA-N 4-chloro-5-methyl-6-phenylpyrimidine Chemical compound CC1=C(Cl)N=CN=C1C1=CC=CC=C1 JXXFPVBMCMWXBN-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
DMEGQEWPMXDRMO-UHFFFAOYSA-N 4-phenylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=CC=CC=2)=N1 DMEGQEWPMXDRMO-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
UZWDCWONPYILKI-UHFFFAOYSA-N n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC1=NC=C(F)C(C=2C=C3N(C(C)C)C(C)=NC3=C(F)C=2)=N1 UZWDCWONPYILKI-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

CA000357364A 1979-08-08 1980-07-30 7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8 Expired CA1137084A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000357364A CA1137084A (fr)	1979-08-08	1980-07-30	7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US6470779A	1979-08-08	1979-08-08
US06/064,707		1979-08-08
CA000357364A CA1137084A (fr)	1979-08-08	1980-07-30	7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8

Publications (1)

Publication Number	Publication Date
CA1137084A true CA1137084A (fr)	1982-12-07

Family

ID=25669122

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000357364A Expired CA1137084A (fr)	1979-08-08	1980-07-30	7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8

Country Status (1)

Country	Link
CA (1)	CA1137084A (fr)

1980
- 1980-07-30 CA CA000357364A patent/CA1137084A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1988-12-06	MZSU	Surrender
2023-05-26	MZSU	Surrender	Effective date: 19881206

Publication	Publication Date	Title
US5502187A (en)	1996-03-26	Pharmaceutically active bicyclic-heterocyclic amines
US5935966A (en)	1999-08-10	Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions
CA1138454A (fr)	1982-12-28	5-(2-imidazoline-2-yl)-aminopyrimidines substituees et methode pour les preparer
EP1718649B1 (fr)	2009-06-10	Derives d'acide imidazo 1,2-c¨pyrimidinylacetique
EP1471057A1 (fr)	2004-10-27	Derivés de l'acid pyrimidinylacétique pour le traitment des maladies associées au CRTH2
US5416211A (en)	1995-05-16	Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines
JPH0853454A (ja)	1996-02-27	薬理活性を有するピロロピリミジン
CA2084490C (fr)	1998-08-25	Procede pour la preparation de pyrrolo[2,3-d]pyrimidines
US5612482A (en)	1997-03-18	Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines
KR20000052540A (ko)	2000-08-25	Ｎ-(아미노-4,6-다이할로피리미딘)포름아마이드의 제조 방법
US4199588A (en)	1980-04-22	6-Phenyl-4H-s-triazolo-[3,4c]-thieno-[2,3e]-1,4-diazepines and salts thereof
CA1246064A (fr)	1988-12-06	Derives de substitution en 8 de 7-phenyl-¬1,2,4\| triazolo¬2,3-c\|pyrimidines-5-amines et amides
US6274734B1 (en)	2001-08-14	Process for making pyrimidine derivatives
CA1224460A (fr)	1987-07-21	.beta.-GLYCOSYL C-NUCLEOSIDES ANTI-LEUCEMIQUES
CA1137084A (fr)	1982-12-07	7-phenyl-1,2,4-triazolo(4,3-c)pyrimidines-5- amines et amides substitues en position 8
US4472400A (en)	1984-09-18	Triazoloquinazolones having antihistaminic and bronchospasmolytic activity
CA1038386A (en)	1978-09-12	Pyrrolo(3,4-d) pyrimidines and methods for their preparation
CA1296323C (fr)	1992-02-25	N-alkylation de l'acide dihydrolysergique
US4405780A (en)	1983-09-20	8-Substituted 7-phenyl-1,2,4,-triazolo[4,3-c]/[2,3-c]pyrimidines-5-amines and amides
US4703049A (en)	1987-10-27	2-(1,2,4-oxadiazol-5-yl) and 2-(1,3,4-thiadiazol-2-yl-imidazo[1,2-a]pyrimidines
US4705787A (en)	1987-11-10	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
Komkov et al.	1995	5-Acetyl-6-amino-4-methylthio-2-phenylpyrimidine and its use in the synthesis of functionalized pyrido [2, 3-d] pyrimidines and pyrimido-[4, 5-d] pyrimidines
US3557115A (en)	1971-01-19	2 - (2 - imidazolin and pyrimidin substituted methylthio) - imidazoles and pyrimidines
US4205169A (en)	1980-05-27	N-[4-Azido-5-(2-ethoxyethyl)-6-phenyl-2-pyrimidinyl]acetamide and congeners
Elnagdi et al.	1977	Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2, 3-a] pyrimidines. A New Ring System