NO803521L - Fremgangsmaate for fremstilling av terapeutisk aktive tiazolo-pyrimidin-karboksamid-derivater - Google Patents

Fremgangsmaate for fremstilling av terapeutisk aktive tiazolo-pyrimidin-karboksamid-derivater

Info

Publication number: NO803521L
Authority: NO; Norway
Prior art keywords: pyrimidine; oxo; ethyl; mmol; cooled
Prior art date: 1979-11-23

Application number

NO803521A

Other languages

English (en)

Norwegian (no)

Inventor

Saul Bernnard 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

1981-05-25

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

1981-05-25 Publication of NO803521L publication Critical patent/NO803521L/no

Links

238000002360 preparation method Methods 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 29
150000001875 compounds Chemical class 0.000 claims abstract description 43
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 27
239000007822 coupling agent Substances 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 4
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
230000009471 action Effects 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 28
230000003266 anti-allergic effect Effects 0.000 abstract description 14
230000000767 anti-ulcer Effects 0.000 abstract description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 181
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 100
239000011541 reaction mixture Substances 0.000 description 74
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 description 65
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 60
239000012043 crude product Substances 0.000 description 59
239000000047 product Substances 0.000 description 59
238000001914 filtration Methods 0.000 description 52
238000001953 recrystallisation Methods 0.000 description 52
238000004458 analytical method Methods 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 37
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 35
239000007789 gas Substances 0.000 description 35
239000007787 solid Substances 0.000 description 32
238000010438 heat treatment Methods 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000000741 silica gel Substances 0.000 description 24
229910002027 silica gel Inorganic materials 0.000 description 24
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
241000700159 Rattus Species 0.000 description 22
238000004090 dissolution Methods 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000010992 reflux Methods 0.000 description 20
238000012360 testing method Methods 0.000 description 19
150000007513 acids Chemical class 0.000 description 17
239000003480 eluent Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 15
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 15
-1 cationic salts Chemical class 0.000 description 15
239000003814 drug Substances 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
206010052428 Wound Diseases 0.000 description 14
208000027418 Wounds and injury Diseases 0.000 description 14
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 14
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
230000005494 condensation Effects 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
238000007363 ring formation reaction Methods 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000009833 condensation Methods 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
238000011282 treatment Methods 0.000 description 11
150000001408 amides Chemical class 0.000 description 10
208000003455 anaphylaxis Diseases 0.000 description 10
229940079593 drug Drugs 0.000 description 10
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 10
210000002784 stomach Anatomy 0.000 description 10
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 9
206010002198 Anaphylactic reaction Diseases 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
159000000000 sodium salts Chemical class 0.000 description 9
230000036783 anaphylactic response Effects 0.000 description 8
229960000265 cromoglicic acid Drugs 0.000 description 8
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 8
239000000543 intermediate Substances 0.000 description 8
238000001556 precipitation Methods 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 7
206010020751 Hypersensitivity Diseases 0.000 description 7
208000025865 Ulcer Diseases 0.000 description 7
239000000908 ammonium hydroxide Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
208000026935 allergic disease Diseases 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
239000012458 free base Substances 0.000 description 6
229960001340 histamine Drugs 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000001665 trituration Methods 0.000 description 6
231100000397 ulcer Toxicity 0.000 description 6
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
239000000043 antiallergic agent Substances 0.000 description 5
239000000427 antigen Substances 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
239000003699 antiulcer agent Substances 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000008103 glucose Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
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 4
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208000007107 Stomach Ulcer Diseases 0.000 description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
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238000002347 injection Methods 0.000 description 4
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QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
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UZWADJYISZVARR-UHFFFAOYSA-N 4-butan-2-yl-1,3-thiazol-2-amine Chemical compound CCC(C)C1=CSC(N)=N1 UZWADJYISZVARR-UHFFFAOYSA-N 0.000 description 3
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239000000739 antihistaminic agent Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
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230000006378 damage Effects 0.000 description 3
HSCHCFKPAQGDPY-UHFFFAOYSA-N diethyl 2-[[(4,5-diethyl-1,3-thiazol-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=NC(CC)=C(CC)S1 HSCHCFKPAQGDPY-UHFFFAOYSA-N 0.000 description 3
KOKDCBPRKLRIOR-UHFFFAOYSA-N diethyl 2-[[(4-tert-butyl-1,3-thiazol-2-yl)amino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=NC(C(C)(C)C)=CS1 KOKDCBPRKLRIOR-UHFFFAOYSA-N 0.000 description 3
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DYWUOAQIROXLHV-UHFFFAOYSA-N 4-pentyl-1,3-thiazol-2-amine Chemical compound CCCCCC1=CSC(N)=N1 DYWUOAQIROXLHV-UHFFFAOYSA-N 0.000 description 2
HNOGSSUZDLBROJ-UHFFFAOYSA-N 5-ethyl-1,3-thiazol-2-amine Chemical compound CCC1=CN=C(N)S1 HNOGSSUZDLBROJ-UHFFFAOYSA-N 0.000 description 2
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MENMPXBUKLPJKR-UHFFFAOYSA-N 5-propan-2-yl-1,3-thiazol-2-amine Chemical compound CC(C)C1=CN=C(N)S1 MENMPXBUKLPJKR-UHFFFAOYSA-N 0.000 description 2
WURBKTNKFMMSGZ-UHFFFAOYSA-N 5-propyl-1,3-thiazol-2-amine Chemical compound CCCC1=CN=C(N)S1 WURBKTNKFMMSGZ-UHFFFAOYSA-N 0.000 description 2
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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

Landscapes

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)

NO803521A 1979-11-23 1980-11-21 Fremgangsmaate for fremstilling av terapeutisk aktive tiazolo-pyrimidin-karboksamid-derivater NO803521L (no)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
NO803521L true NO803521L (no)	1981-05-25

Family

ID=22258306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO803521A NO803521L (no)	1979-11-23	1980-11-21	Fremgangsmaate for fremstilling av terapeutisk aktive tiazolo-pyrimidin-karboksamid-derivater

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)	DE3043979C2 (fr)
DK (1)	DK151811C (fr)
EG (1)	EG14929A (fr)
ES (1)	ES8203363A1 (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
DE68926473T2 (de) *	1988-03-28	1996-10-02	Janssen Pharmaceutica Nv	Mittel zur Konservierung oder Wiederherstellung der gesunden Haut
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 AR AR283276A patent/AR228859A1/es active
- 1980-11-18 GB GB8036904A patent/GB2063862B/en not_active Expired
- 1980-11-18 CS CS807820A patent/CS241476B2/cs unknown
- 1980-11-18 HU HU80802755A patent/HU179091B/hu not_active IP Right Cessation
- 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 YU YU2950/80A patent/YU41953B/xx unknown
- 1980-11-20 NZ NZ195596A patent/NZ195596A/en unknown
- 1980-11-21 FR FR8024822A patent/FR2470132A1/fr active Granted
- 1980-11-21 IT IT8026176A patent/IT1209373B/it active
- 1980-11-21 NO NO803521A patent/NO803521L/no unknown
- 1980-11-21 ES ES497066A patent/ES8203363A1/es not_active Expired
- 1980-11-21 CA CA000365258A patent/CA1143731A/fr not_active Expired
- 1980-11-21 SE SE8008189A patent/SE448732B/sv not_active IP Right Cessation
- 1980-11-21 IE IE2418/80A patent/IE50404B1/en unknown
- 1980-11-21 FI FI803628A patent/FI67706C/fi not_active IP Right Cessation
- 1980-11-21 NL NLAANVRAGE8006362,A patent/NL182565C/xx not_active IP Right Cessation
- 1980-11-21 DE DE3043979A patent/DE3043979C2/de not_active Expired
- 1980-11-21 IL IL61535A patent/IL61535A/xx unknown
- 1980-11-21 LU LU82950A patent/LU82950A1/fr unknown
- 1980-11-21 JP JP16450280A patent/JPS5687586A/ja active Granted
- 1980-11-21 ZA ZA00807293A patent/ZA807293B/xx unknown
- 1980-11-21 DE DE3050491A patent/DE3050491C2/de not_active Expired
- 1980-11-21 PT PT72090A patent/PT72090B/pt not_active IP Right Cessation
- 1980-11-21 AU AU64595/80A patent/AU520995B2/en not_active Ceased
- 1980-11-21 AT AT0570780A patent/AT380883B/de not_active IP Right Cessation
- 1980-11-21 PH PH24891A patent/PH16666A/en unknown
- 1980-11-21 GT GT198066458A patent/GT198066458A/es unknown
- 1980-11-21 DD DD80225391A patent/DD154608A5/de not_active IP Right Cessation
- 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
PT72090A (en)	1980-12-01
FI67706B (fi)	1985-01-31
FR2470132A1 (fr)	1981-05-29
DE3043979A1 (de)	1981-09-03
PL132354B1 (en)	1985-02-28
ZA807293B (en)	1981-12-30
PL228008A1 (fr)	1981-12-11
IL61535A (en)	1984-06-29
IE50404B1 (en)	1986-04-16
CH649299A5 (fr)	1985-05-15
DK413180A (da)	1981-05-24
FI803628L (fi)	1981-05-24
AR231296A1 (es)	1984-10-31
DK151811B (da)	1988-01-04
NL8006362A (nl)	1981-06-16
CS782080A2 (en)	1985-06-13
DD154608A5 (de)	1982-04-07
GT198066458A (es)	1982-05-15
CA1143731A (fr)	1983-03-29
AT380883B (de)	1986-07-25
GR72132B (fr)	1983-09-19
IN154926B (fr)	1984-12-22
SE448732B (sv)	1987-03-16
KR830004322A (ko)	1983-07-09
SU1042620A3 (ru)	1983-09-15
IT8026176A0 (it)	1980-11-21
HU179091B (en)	1982-08-28
FI67706C (fi)	1985-05-10
YU41953B (en)	1988-02-29
AR228859A1 (es)	1983-04-29
SE8008189L (sv)	1981-05-24
PT72090B (en)	1981-09-29
LU82950A1 (fr)	1981-06-04
ES497066A0 (es)	1982-04-01
IT1209373B (it)	1989-07-16
GB2063862A (en)	1981-06-10
GB2063862B (en)	1983-06-22
IE802418L (en)	1981-05-23
DE3050491C2 (de)	1985-10-10
YU295080A (en)	1983-06-30
NL182565C (nl)	1988-04-05
PH16666A (en)	1983-12-13
CS241476B2 (en)	1986-03-13
ATA570780A (de)	1985-12-15
EG14929A (en)	1989-01-30
IL61535A0 (en)	1980-12-31
JPS617432B2 (fr)	1986-03-06
BE886319A (fr)	1981-05-25
FR2470132B1 (fr)	1983-07-29
AU6459580A (en)	1981-05-28
ES8203363A1 (es)	1982-04-01
DE3043979C2 (de)	1986-08-21
NZ195596A (en)	1984-05-31
AU520995B2 (en)	1982-03-11
NL182565B (nl)	1987-11-02
DK151811C (da)	1988-06-06
JPS5687586A (en)	1981-07-16

Publication	Publication Date	Title
FI96857C (fi)	1996-09-10	Menetelmä valmistaa farmakologisesti käyttökelpoista tiatsoliyhdistettä
AU656859B2 (en)	1995-02-16	Aryl group- or aromatic heterocyclic group-substituted aminoquinolone derivatives and anti-HIV agent
HU190408B (en)	1986-09-29	Process for producing pharmaceutical preparations comprising new benzimidazole-derivatives
NO162073B (no)	1989-07-24	Analogifremgangsmaate for fremstilling av farmakologiske aktive heterocykliske forbindelser.
FI75821B (fi)	1988-04-29	Foerfarande foer framstaellning av terapeutiskt aktiva 2-guanidino-4-heteroaryltiazoler.
US4704387A (en)	1987-11-03	N-benzyl, phenethyl, methoxyethyl or allyl substituted benzylphthalazinones having antiallergic and antihistamine action
CA2129429A1 (fr)	1993-08-14	(azaaromaticalkoxy) indoles utilises comme inhibiteurs de la biosynthese de la leucotriene
KR900003368B1 (ko)	1990-05-16	신규한 인데노티아졸 유도체의 제조방법
US4734413A (en)	1988-03-29	Substituted 1,2,4-triazolo[1,5-A]triazines as bronchodilators
DK153950B (da)	1988-09-26	Analogifremgangsmaade til fremstilling af quinolylguanidiner eller derivater deraf
FI91752C (fi)	1994-08-10	Menetelmä terapeuttisesti käyttökelpoisten aryylipiperatsinyylialkyleenifenyylisubstituoitujen heterosyklisten yhdisteiden valmistamiseksi
NO822918L (no)	1983-03-01	Nye imidazokinazolinderivater.
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
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
US4705787A (en)	1987-11-10	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
US4414388A (en)	1983-11-08	1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
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
FI91871C (fi)	1994-08-25	Menetelmä lääkeaineina käyttökelpoisten 1H-imidatso/1,2-b/-pyratsolin johdannaisten valmistamiseksi
NO163896B (no)	1990-04-30	Analogifremgangsmaate ved fremstilling av terapeutisk aktive spiro-(1,8)-nafthyridin-dioner.
SE414175B (sv)	1980-07-14	Analogiflrfarande for framstellning av anti-allergiska n-(-tetranzolyl)-pyrimido (1,2-a) kinolin-2-karboxamider
US4491587A (en)	1985-01-01	Tetrazole derivatives
FI71158C (fi)	1986-11-24	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-xo-1h-tiazolo/3,2-a/pyrimidin-2-karboxylsyror
CA1051891A (fr)	1979-04-03	Derives de triazolocycloalkylthiadiazine