CH645898A5 - Gegebenenfalls 8-substituierte 7-phenyl-1,2,4-triazolo (1,5-c)-pyrimidin-5-amine und -amide. - Google Patents

Gegebenenfalls 8-substituierte 7-phenyl-1,2,4-triazolo (1,5-c)-pyrimidin-5-amine und -amide. Download PDF

Info

Publication number: CH645898A5
Authority: CH; Switzerland
Prior art keywords: radical; carbon atoms; phenyl; formula; triazolo
Prior art date: 1979-08-08

Application number

CH603080A

Other languages

German (de)

English (en)

Inventor

Hans A Wagner

Original Assignee

Searle & Co

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

1980-08-08

Publication date

1984-10-31

1980-08-08 Application filed by Searle & Co filed Critical Searle & Co

1984-10-31 Publication of CH645898A5 publication Critical patent/CH645898A5/de

Links

-1 8-SUBSTITUTED 7-PHENYL-1,2,4-TRIAZOLO (1,5-C) -PYRIMIDINE-5-AMINE Chemical class 0.000 title claims description 26
150000001408 amides Chemical class 0.000 title description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
AVLOEGSIJCOHSS-UHFFFAOYSA-N n-(8-methyl-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-yl)acetamide Chemical compound CC=1C2=NC=NN2C(NC(=O)C)=NC=1C1=CC=CC=C1 AVLOEGSIJCOHSS-UHFFFAOYSA-N 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
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 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical class NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
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 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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 2
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XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
239000003708 ampul Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
235000005687 corn oil Nutrition 0.000 description 2
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239000002934 diuretic Substances 0.000 description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
229960002003 hydrochlorothiazide Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
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239000002808 molecular sieve Substances 0.000 description 2
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WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
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LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
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LFGNMJSUWYTYMS-UHFFFAOYSA-N 4-chloro-5-(2-ethoxyethyl)-6-phenylpyrimidin-2-amine Chemical compound CCOCCC1=C(Cl)N=C(N)N=C1C1=CC=CC=C1 LFGNMJSUWYTYMS-UHFFFAOYSA-N 0.000 description 1
FYDXFOVDFWZZNU-UHFFFAOYSA-N 4-chloro-5-methyl-6-phenylpyrimidin-2-amine Chemical compound CC1=C(Cl)N=C(N)N=C1C1=CC=CC=C1 FYDXFOVDFWZZNU-UHFFFAOYSA-N 0.000 description 1
FTZKVVCULMKDTL-UHFFFAOYSA-N 4-chloro-6-phenyl-5-prop-2-ynylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=C(CC#C)C(C=2C=CC=CC=2)=N1 FTZKVVCULMKDTL-UHFFFAOYSA-N 0.000 description 1
OZSPQIXKOVJJGE-UHFFFAOYSA-N 8-(2-ethoxyethyl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound N1=C(N)N2N=CN=C2C(CCOCC)=C1C1=CC=CC=C1 OZSPQIXKOVJJGE-UHFFFAOYSA-N 0.000 description 1
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229920000609 methyl cellulose Polymers 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
AOXKNJMJBRZSRZ-UHFFFAOYSA-N n-(4-chloro-5-methyl-6-phenylpyrimidin-2-yl)acetamide Chemical compound CC(=O)NC1=NC(Cl)=C(C)C(C=2C=CC=CC=2)=N1 AOXKNJMJBRZSRZ-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
RSZDZHKPBDENGK-UHFFFAOYSA-N n-[4-chloro-5-(2-ethoxyethyl)-6-phenylpyrimidin-2-yl]acetamide Chemical compound CCOCCC1=C(Cl)N=C(NC(C)=O)N=C1C1=CC=CC=C1 RSZDZHKPBDENGK-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
238000013021 overheating Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013772 propylene glycol Nutrition 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
150000003254 radicals Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
229960003010 sodium sulfate Drugs 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 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
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH603080A 1979-08-08 1980-08-08 Gegebenenfalls 8-substituierte 7-phenyl-1,2,4-triazolo (1,5-c)-pyrimidin-5-amine und -amide. CH645898A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6470779A	1979-08-08	1979-08-08

Publications (1)

Publication Number	Publication Date
CH645898A5 true CH645898A5 (de)	1984-10-31

Family

ID=22057763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH603080A CH645898A5 (de)	1979-08-08	1980-08-08	Gegebenenfalls 8-substituierte 7-phenyl-1,2,4-triazolo (1,5-c)-pyrimidin-5-amine und -amide.

Country Status (7)

Country	Link
JP (1)	JPS5632479A (da)
AU (1)	AU531507B2 (da)
CA (2)	CA1246063A (da)
CH (1)	CH645898A5 (da)
DE (1)	DE3029871C2 (da)
FR (1)	FR2463143A1 (da)
GB (1)	GB2056449A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3029871C2 (de)	1979-08-08	1987-01-15	G.D. Searle & Co., Skokie, Ill.	8-(2-Ethoxyethyl)-7-phenyl-1,2,4-triazolo[1,5-c]pyrimidin-5-amin, Verfahren zu dessen Herstellung und pharmazeutische Zubereitung, die diese Verbindung enthält

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK135184A (da) *	1983-03-03	1984-10-10	Riker Laboratories Inc	Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner
US4532242A (en) *	1983-05-02	1985-07-30	Riker Laboratories, Inc.	Substituted triazolo[4,3-c]pyrimidines
US4528288A (en) *	1983-05-02	1985-07-09	Riker Laboratories, Inc.	Substituted triazolo[1,5-c]pyrimidines
US4483987A (en) *	1983-06-20	1984-11-20	G. D. Searle & Co.	8-Substituted 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines and amides
US4866063A (en) *	1988-12-22	1989-09-12	G. D. Searle & Co.	Diol metabolites of 7-phenyl-1,2,4-triazolo[2,3-c]pyrimidines-5-amines
TW440563B (en) *	1996-05-23	2001-06-16	Hoffmann La Roche	Aryl pyrimidine derivatives and a pharmaceutical composition thereof
US5952331A (en) *	1996-05-23	1999-09-14	Syntex (Usa) Inc.	Aryl pyrimidine derivatives
US5958934A (en) *	1996-05-23	1999-09-28	Syntex (U.S.A.) Inc.	Aryl pyrimidine derivatives and uses thereof
EP2638018A1 (en)	2010-11-09	2013-09-18	Cellzome Limited	Pyridine compounds and aza analogues thereof as tyk2 inhibitors
EP3950064A4 (en) *	2019-04-03	2023-01-04	Tera Stone Co., Ltd	THYMINE NUCLEOBASE BASED TRIAZOLOPYRIMIDINES AND PROCESS FOR THEIR PRODUCTION

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1205144A (fr) *	1957-06-14	1960-01-29	Farmaceutici Italia	Procédé pour la synthèse de 7-méthyl-s. triazol (4, 3-c) pyrimidines substituéesen position 5
US3284542A (en)	1963-03-22	1966-11-08	Rexall Drug Chemical	Preparation of high impact compositions from vinyl aromatic monomers and rubbery diolefin polymers
US3244715A (en)	1964-10-30	1966-04-05	Smith Kline French Lab	Phenylimidazo [4, 5-d] pyridazines
US3461123A (en)	1968-04-12	1969-08-12	Merck & Co Inc	1h-imidazo(4,5-b)pyrazin-2-ones and processes for their preparation
AU531507B2 (en)	1979-08-08	1983-08-25	G.D. Searle & Co.	8-substituted 7-phenyl-1,2,4-triazolo(4,3-c) pyrimidines -5-amines and amides

1980
- 1980-08-07 AU AU61153/80A patent/AU531507B2/en not_active Ceased
- 1980-08-07 DE DE3029871A patent/DE3029871C2/de not_active Expired
- 1980-08-07 GB GB8025795A patent/GB2056449A/en not_active Withdrawn
- 1980-08-08 JP JP10910380A patent/JPS5632479A/ja active Granted
- 1980-08-08 CH CH603080A patent/CH645898A5/de not_active IP Right Cessation
- 1980-08-08 FR FR8017582A patent/FR2463143A1/fr active Granted
1986
- 1986-12-04 CA CA000524601A patent/CA1246063A/en not_active Expired
- 1986-12-04 CA CA000524602A patent/CA1246064B/en not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3029871C2 (de)	1979-08-08	1987-01-15	G.D. Searle & Co., Skokie, Ill.	8-(2-Ethoxyethyl)-7-phenyl-1,2,4-triazolo[1,5-c]pyrimidin-5-amin, Verfahren zu dessen Herstellung und pharmazeutische Zubereitung, die diese Verbindung enthält

Also Published As

Publication number	Publication date
GB2056449A (en)	1981-03-18
AU6115380A (en)	1981-02-12
CA1246064A (en)	1988-12-06
CA1246063B (en)	1988-12-06
DE3029871A1 (de)	1981-02-26
CA1246064B (en)	1988-12-06
FR2463143B1 (da)	1983-12-16
CA1246063A (en)	1988-12-06
JPH029592B2 (da)	1990-03-02
JPS5632479A (en)	1981-04-01
DE3029871C2 (de)	1987-01-15
AU531507B2 (en)	1983-08-25
FR2463143A1 (fr)	1981-02-20

Legal Events

Date	Code	Title	Description
1993-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE60117972T2 (de)	2006-11-23	Neue kristalline form einer triazolo(4,5-d)pyrimidin-verbindung
DE60319255T2 (de)	2009-03-05	Pyrimidoverbindungen mit antiproliferativer wirkung
EP0005205B1 (de)	1981-09-09	Substituierte 5,6-Dimethylpyrrolo(2,3-d)pyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69926665T2 (de)	2006-06-08	Azolo-Pyrimidine
DE69603240T2 (de)	2000-01-05	Neue deazapurinderivate; eine neue klasse von crf1-spezifischen liganden
DE1620740C3 (de)	1979-05-10	Substituierte Tetrahydro-6-Sulfamyl-chinazolinone und diese Verbindungen enthaltende pharmazeutische Präparate
DE60128457T2 (de)	2008-01-17	1,5-DISUBSTITUIERTE 3,4-DIHYDRO-1H-4,5-DöPYRIMIDIN-2-ON-VERBINDUNGEN UND IHRE VERWENDUNG IN DER BEHANDLUNG VON DURCH CSBP/P38 KINASE BEEINFLUSSTEN KRANKHEITEN
DE2502966A1 (de)	1975-07-31	Neue derivate von 1,7-dihydro-2h- pyrazolo(4',3' zu 5,6)pyrido(4,3-d)pyrimidin-2,4-(3h)-dionen
US3930005A (en)	1975-12-30	Antiinflammatory agents and their use
EP0682027A1 (de)	1995-11-15	Pyrrolopyrimidinderivate mit antiproliferativer Wirkung
DE3145287A1 (de)	1983-05-19	Pyrrolo (2.3-d)pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE2700091A1 (de)	1977-07-14	1-(substit.-amino)alkanoyl-2-(dibenzoxazepin-10-carbonyl)-hydrazine und deren derivate
DE3029871A1 (de)	1981-02-26	8-substituierte 7-phenyl-1,2,4-triazolo eckige klammer auf 4,3-c eckige klammer zu pyrimidin-5-amine und -amide
DE2710242A1 (de)	1977-09-22	5-eckige klammer auf 1,1-diphenyl- 3-(5- oder 6-hydroxy-2-azabicyclo eckige klammer auf 2,2,2 eckige klammer zu oct-2-yl)propyl eckige klammer zu -2- alkyl-1,3,4-oxadiazole und verwandte verbindungen
CH622019A5 (en)	1981-03-13	Process for the preparation of aminotriazolobenzodiazepines
EP0180115A2 (de)	1986-05-07	1,2,4-Triazolo-carbamate und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
KR20010112487A (ko)	2001-12-20	이미다조디아제핀 유도체
DE2913295C2 (da)	1988-09-22
DE60004362T2 (de)	2004-02-26	Thiazolopyrimidine verwendbar als TNF-Alpha Inhibitoren
DE3337925C2 (de)	1994-11-24	N-(6-Aminopurinyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazin-3-carboxamid-1,1-dioxid, Verfahren zu dessen Herstellung und seine Verwendung
DE2316728C2 (da)	1988-09-08
DE3709699C2 (de)	1996-09-05	5-Fluoruracil-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2456311A1 (de)	1975-06-05	Benzodiazepinderivate
US3389136A (en)	1968-06-18	10-(3-dimethylaminopropyl)-3-azapheno-thiazine and derivatives thereof
AT367054B (de)	1982-05-25	Verfahren zur herstellung von mono-alkenyl-dialkylxanthinen

CH645898A5 - Gegebenenfalls 8-substituierte 7-phenyl-1,2,4-triazolo (1,5-c)-pyrimidin-5-amine und -amide. - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=22057763

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (10)

Family Cites Families (5)

Cited By (1)

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