SE448732B - N-(5-tetrazolyl)-1-oxo-1h-tiazolo /3,2-a/-pyrimidin-2-karboxamider med antiallergisk och antiulceros verkan samt motsvarande 2-karboxylsyror - Google Patents

N-(5-tetrazolyl)-1-oxo-1h-tiazolo /3,2-a/-pyrimidin-2-karboxamider med antiallergisk och antiulceros verkan samt motsvarande 2-karboxylsyror

Info

Publication number: SE448732B
Authority: SE; Sweden
Prior art keywords: oxo; pyrimidine; ethyl; mmol; cooled
Prior art date: 1979-11-23

Application number

SE8008189A

Other languages

English (en)

Swedish (sv)

Other versions

SE8008189L (sv

Inventor

S B Kadin

Original Assignee

Pfizer

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.)

1979-11-23

Filing date

1980-11-21

Publication date

1987-03-16

1980-11-21 Application filed by Pfizer filed Critical Pfizer

1981-05-24 Publication of SE8008189L publication Critical patent/SE8008189L/xx

1987-03-16 Publication of SE448732B publication Critical patent/SE448732B/sv

Links

-1 5-TETRAZOLYL Chemical class 0.000 title description 78
239000002253 acid Substances 0.000 title description 38
230000000694 effects Effects 0.000 title description 29
230000003266 anti-allergic effect Effects 0.000 title description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 68
150000001875 compounds Chemical class 0.000 claims description 51
229910052757 nitrogen Inorganic materials 0.000 claims description 51
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
239000001257 hydrogen Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
125000002091 cationic group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 197
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 116
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 106
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
239000000203 mixture Substances 0.000 description 82
239000011541 reaction mixture Substances 0.000 description 80
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 description 64
239000000047 product Substances 0.000 description 59
239000012043 crude product Substances 0.000 description 56
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 47
238000004458 analytical method Methods 0.000 description 46
229910052799 carbon Inorganic materials 0.000 description 44
FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 description 38
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 37
239000007787 solid Substances 0.000 description 35
229910001868 water Inorganic materials 0.000 description 35
238000001953 recrystallisation Methods 0.000 description 34
239000007789 gas Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 31
239000000499 gel Substances 0.000 description 30
238000010438 heat treatment Methods 0.000 description 28
239000002904 solvent Substances 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 26
238000004090 dissolution Methods 0.000 description 26
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000000741 silica gel Substances 0.000 description 25
229910002027 silica gel Inorganic materials 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
241000700159 Rattus Species 0.000 description 23
238000012360 testing method Methods 0.000 description 23
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical class NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 20
239000003480 eluent Substances 0.000 description 20
150000003839 salts Chemical class 0.000 description 20
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 20
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150000007513 acids Chemical class 0.000 description 18
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239000004480 active ingredient Substances 0.000 description 17
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QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 16
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238000002844 melting Methods 0.000 description 14
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
239000002775 capsule Substances 0.000 description 12
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150000002148 esters Chemical class 0.000 description 11
238000007363 ring formation reaction Methods 0.000 description 11
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
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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 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
238000001816 cooling Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
230000005764 inhibitory process Effects 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
208000003455 anaphylaxis Diseases 0.000 description 8
238000010171 animal model Methods 0.000 description 8
230000000767 anti-ulcer Effects 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 7
206010002198 Anaphylactic reaction Diseases 0.000 description 7
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
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230000036783 anaphylactic response Effects 0.000 description 6
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239000007864 aqueous solution Substances 0.000 description 6
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229960000265 cromoglicic acid Drugs 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000012458 free base Substances 0.000 description 6
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150000002500 ions Chemical class 0.000 description 6
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150000001412 amines Chemical class 0.000 description 5
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RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 4
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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 4
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SIHBOLQMULXEHS-UHFFFAOYSA-N 1-chloro-1,1,2,2,2-pentafluoroethane;1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl.FC(F)(Cl)C(F)(F)Cl SIHBOLQMULXEHS-UHFFFAOYSA-N 0.000 description 3
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GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 3
CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Thiazole And Isothizaole Compounds (AREA)

SE8008189A 1979-11-23 1980-11-21 N-(5-tetrazolyl)-1-oxo-1h-tiazolo /3,2-a/-pyrimidin-2-karboxamider med antiallergisk och antiulceros verkan samt motsvarande 2-karboxylsyror SE448732B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US9663179A	1979-11-23	1979-11-23

Publications (2)

Publication Number	Publication Date
SE8008189L SE8008189L (sv)	1981-05-24
SE448732B true SE448732B (sv)	1987-03-16

Family

ID=22258306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8008189A SE448732B (sv)	1979-11-23	1980-11-21	N-(5-tetrazolyl)-1-oxo-1h-tiazolo /3,2-a/-pyrimidin-2-karboxamider med antiallergisk och antiulceros verkan samt motsvarande 2-karboxylsyror

Country Status (35)

Country	Link
JP (1)	JPS5687586A (fr)
KR (1)	KR830004322A (fr)
AR (2)	AR228859A1 (fr)
AT (1)	AT380883B (fr)
AU (1)	AU520995B2 (fr)
BE (1)	BE886319A (fr)
CA (1)	CA1143731A (fr)
CH (1)	CH649299A5 (fr)
CS (1)	CS241476B2 (fr)
DD (1)	DD154608A5 (fr)
DE (2)	DE3050491C2 (fr)
DK (1)	DK151811C (fr)
EG (1)	EG14929A (fr)
ES (1)	ES497066A0 (fr)
FI (1)	FI67706C (fr)
FR (1)	FR2470132A1 (fr)
GB (1)	GB2063862B (fr)
GR (1)	GR72132B (fr)
GT (1)	GT198066458A (fr)
HU (1)	HU179091B (fr)
IE (1)	IE50404B1 (fr)
IL (1)	IL61535A (fr)
IN (1)	IN154926B (fr)
IT (1)	IT1209373B (fr)
LU (1)	LU82950A1 (fr)
NL (1)	NL182565C (fr)
NO (1)	NO803521L (fr)
NZ (1)	NZ195596A (fr)
PH (1)	PH16666A (fr)
PL (1)	PL132354B1 (fr)
PT (1)	PT72090B (fr)
SE (1)	SE448732B (fr)
SU (1)	SU1042620A3 (fr)
YU (1)	YU41953B (fr)
ZA (1)	ZA807293B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8300728D0 (en) *	1983-01-12	1983-02-16	Erba Farmitalia	Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives
US4457932A (en) *	1983-07-22	1984-07-03	Bristol-Myers Company	Anti-ulcer agents
GB8422916D0 (en) *	1984-09-11	1984-10-17	May & Baker Ltd	Compositions of matter
JP2690742B2 (ja) *	1987-03-30	1997-12-17	第一製薬株式会社	複素環アミン誘導体
NZ228447A (en) *	1988-03-28	1990-08-28	Janssen Pharmaceutica Nv	Cosmetic or pharmaceutical composition possessing serotonin antogonistic activity
TWI500623B (zh) *	2009-10-13	2015-09-21	Torrent Pharmaceuticals Ltd	新穎稠合噻唑及噁唑嘧啶酮

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1331059A (en)	1971-04-19	1973-09-19	Lilly Industries Ltd	Pyrimidotriazinone compounds
US4041163A (en) *	1976-03-29	1977-08-09	Pfizer Inc.	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents
DE2810863A1 (de) *	1978-03-13	1979-09-27	Boehringer Mannheim Gmbh	1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazol-derivate und verfahren zu ihrer herstellung
US4223031A (en) *	1978-05-05	1980-09-16	Mead Johnson & Company	Azolopyrimidinones

1980
- 1980-09-30 DK DK413180A patent/DK151811C/da not_active IP Right Cessation
- 1980-10-15 IN IN760/DEL/80A patent/IN154926B/en unknown
- 1980-11-17 SU SU803212053A patent/SU1042620A3/ru active
- 1980-11-18 GB GB8036904A patent/GB2063862B/en not_active Expired
- 1980-11-18 HU HU80802755A patent/HU179091B/hu not_active IP Right Cessation
- 1980-11-18 AR AR283276A patent/AR228859A1/es active
- 1980-11-18 CS CS807820A patent/CS241476B2/cs unknown
- 1980-11-19 EG EG723/80A patent/EG14929A/xx active
- 1980-11-19 CH CH8567/80A patent/CH649299A5/fr not_active IP Right Cessation
- 1980-11-20 GR GR63413A patent/GR72132B/el unknown
- 1980-11-20 NZ NZ195596A patent/NZ195596A/en unknown
- 1980-11-20 YU YU2950/80A patent/YU41953B/xx unknown
- 1980-11-21 NL NLAANVRAGE8006362,A patent/NL182565C/xx not_active IP Right Cessation
- 1980-11-21 NO NO803521A patent/NO803521L/no unknown
- 1980-11-21 ZA ZA00807293A patent/ZA807293B/xx unknown
- 1980-11-21 CA CA000365258A patent/CA1143731A/fr not_active Expired
- 1980-11-21 PT PT72090A patent/PT72090B/pt not_active IP Right Cessation
- 1980-11-21 DD DD80225391A patent/DD154608A5/de not_active IP Right Cessation
- 1980-11-21 IL IL61535A patent/IL61535A/xx unknown
- 1980-11-21 IE IE2418/80A patent/IE50404B1/en unknown
- 1980-11-21 DE DE3050491A patent/DE3050491C2/de not_active Expired
- 1980-11-21 SE SE8008189A patent/SE448732B/sv not_active IP Right Cessation
- 1980-11-21 ES ES497066A patent/ES497066A0/es active Granted
- 1980-11-21 GT GT198066458A patent/GT198066458A/es unknown
- 1980-11-21 AT AT0570780A patent/AT380883B/de not_active IP Right Cessation
- 1980-11-21 AU AU64595/80A patent/AU520995B2/en not_active Ceased
- 1980-11-21 FR FR8024822A patent/FR2470132A1/fr active Granted
- 1980-11-21 JP JP16450280A patent/JPS5687586A/ja active Granted
- 1980-11-21 LU LU82950A patent/LU82950A1/fr unknown
- 1980-11-21 FI FI803628A patent/FI67706C/fi not_active IP Right Cessation
- 1980-11-21 IT IT8026176A patent/IT1209373B/it active
- 1980-11-21 PH PH24891A patent/PH16666A/en unknown
- 1980-11-21 DE DE3043979A patent/DE3043979C2/de not_active Expired
- 1980-11-22 KR KR1019800004474A patent/KR830004322A/ko not_active Ceased
- 1980-11-22 PL PL1980228008A patent/PL132354B1/pl unknown
- 1980-11-24 BE BE0/202915A patent/BE886319A/fr not_active IP Right Cessation
1982
- 1982-09-13 AR AR290628A patent/AR231296A1/es active

Also Published As

Publication number	Publication date
LU82950A1 (fr)	1981-06-04
PL132354B1 (en)	1985-02-28
NO803521L (no)	1981-05-25
NL182565C (nl)	1988-04-05
NZ195596A (en)	1984-05-31
FI67706C (fi)	1985-05-10
IL61535A (en)	1984-06-29
GB2063862B (en)	1983-06-22
ES8203363A1 (es)	1982-04-01
PH16666A (en)	1983-12-13
CS241476B2 (en)	1986-03-13
JPS617432B2 (fr)	1986-03-06
SU1042620A3 (ru)	1983-09-15
KR830004322A (ko)	1983-07-09
CH649299A5 (fr)	1985-05-15
AR231296A1 (es)	1984-10-31
PL228008A1 (fr)	1981-12-11
DE3050491C2 (de)	1985-10-10
IN154926B (fr)	1984-12-22
DK151811B (da)	1988-01-04
AT380883B (de)	1986-07-25
IL61535A0 (en)	1980-12-31
SE8008189L (sv)	1981-05-24
DE3043979C2 (de)	1986-08-21
YU41953B (en)	1988-02-29
AU520995B2 (en)	1982-03-11
PT72090A (en)	1980-12-01
GB2063862A (en)	1981-06-10
JPS5687586A (en)	1981-07-16
FI803628L (fi)	1981-05-24
CS782080A2 (en)	1985-06-13
CA1143731A (fr)	1983-03-29
DK413180A (da)	1981-05-24
AU6459580A (en)	1981-05-28
GR72132B (fr)	1983-09-19
FI67706B (fi)	1985-01-31
PT72090B (en)	1981-09-29
AR228859A1 (es)	1983-04-29
ATA570780A (de)	1985-12-15
DK151811C (da)	1988-06-06
DE3043979A1 (de)	1981-09-03
NL8006362A (nl)	1981-06-16
GT198066458A (es)	1982-05-15
IE802418L (en)	1981-05-23
YU295080A (en)	1983-06-30
ZA807293B (en)	1981-12-30
DD154608A5 (de)	1982-04-07
NL182565B (nl)	1987-11-02
HU179091B (en)	1982-08-28
IE50404B1 (en)	1986-04-16
ES497066A0 (es)	1982-04-01
IT1209373B (it)	1989-07-16
FR2470132A1 (fr)	1981-05-29
FR2470132B1 (fr)	1983-07-29
EG14929A (en)	1989-01-30
IT8026176A0 (it)	1980-11-21
BE886319A (fr)	1981-05-25

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SU986297A3 (ru)	1982-12-30	Способ получени производных 5-/4-диарилметил/-1-пиперазинилалкилбензимидазола или их солей
US4603203A (en)	1986-07-29	3-aminopyrazolo[3,4-d]pyrimidine derivatives and production thereof
HU211557A9 (en)	1995-12-28	Thiazole derivatives, processes for production thereof and pharmaceutical compositions comprising the same
HU179492B (en)	1982-10-28	Process for producing 1,2,4-thiadiasole derivatives
FI75821B (fi)	1988-04-29	Foerfarande foer framstaellning av terapeutiskt aktiva 2-guanidino-4-heteroaryltiazoler.
EP0391644B1 (fr)	1996-06-19	Dérivés de rhodanine arylsubstitués
US4734413A (en)	1988-03-29	Substituted 1,2,4-triazolo[1,5-A]triazines as bronchodilators
US4435407A (en)	1984-03-06	Certain substituted β-oxo-α-carbamoylpyrrolepropionitriles
US4141899A (en)	1979-02-27	4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridine derivatives
CA1143731A (fr)	1983-03-29	1-oxo-1h-tetrazolo¬3,2-a\| pyrimidine-2- carboxylate, compose antiallergique et anti-ulceres
US3468888A (en)	1969-09-23	2-substituted pyrimido(1,2-a) benzimidazoles
US4705787A (en)	1987-11-10	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
US4423048A (en)	1983-12-27	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
US4535081A (en)	1985-08-13	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
EP0316790B1 (fr)	1993-08-11	Dérivés de rhodanine, procédé de préparation, leur utilisation et les compositions pharmaceutiques les contenant
US4414388A (en)	1983-11-08	1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
US4297365A (en)	1981-10-27	Benzimidazoles and pharmaceutical preparations containing such compounds
CA1088064A (fr)	1980-10-21	Obtention de 1,1-dioxydes de 2,5-dihydro-1,2- thiazino[5,6-b]indol-3-carboxamides et de leurs derives pharmaceutiques
US3898218A (en)	1975-08-05	Process for the preparation of substituted pyrano (3,2-c) (1,2)benzothiazine 6,6-dioxides
EP0081955B1 (fr)	1987-01-21	Composés hétérocycliques benzo-condensés
US4269774A (en)	1981-05-26	Thiazolo[5,4-d][2]benzazepines
US4761474A (en)	1988-08-02	3-(1H-tetrazol-5-yl)thieno[2,3-d]pyrimidin-4(3H)-ones
FI71158C (fi)	1986-11-24	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-xo-1h-tiazolo/3,2-a/pyrimidin-2-karboxylsyror
US3966716A (en)	1976-06-29	2H-1,3,2-dioxaborino-[5,4-c]-1,2-benzo-thiazine 6,6-dioxides
EP0003360A1 (fr)	1979-08-08	Azathianaphtalènes, procédé pour leur préparation, préparations pharmaceutiques les contenant et leur utilisation