PL106659B1 - Sposob wytwarzania nowych pochodnych pirazolo/1,5-c/chinazoliny - Google Patents
Sposob wytwarzania nowych pochodnych pirazolo/1,5-c/chinazoliny Download PDFInfo
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- PL106659B1 PL106659B1 PL1977199270A PL19927077A PL106659B1 PL 106659 B1 PL106659 B1 PL 106659B1 PL 1977199270 A PL1977199270 A PL 1977199270A PL 19927077 A PL19927077 A PL 19927077A PL 106659 B1 PL106659 B1 PL 106659B1
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- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
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- 239000000243 solution Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 239000012043 crude product Substances 0.000 description 31
- 239000002244 precipitate Substances 0.000 description 27
- -1 methoxyl group Chemical group 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
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- 239000000203 mixture Substances 0.000 description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 238000000354 decomposition reaction Methods 0.000 description 6
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 3
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- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
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- 230000000172 allergic effect Effects 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- 239000002249 anxiolytic agent Substances 0.000 description 1
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- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
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- WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZUOCMXBAJIQHD-UHFFFAOYSA-N hex-5-yn-2-ol Chemical compound CC(O)CCC#C FZUOCMXBAJIQHD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OFWAZHHHDNXFTI-UHFFFAOYSA-N n'-(4-chloro-7-methoxy-2-oxoindol-3-yl)-4-methylbenzenesulfonohydrazide Chemical compound O=C1N=C2C(OC)=CC=C(Cl)C2=C1NNS(=O)(=O)C1=CC=C(C)C=C1 OFWAZHHHDNXFTI-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- LXKRETAGISZJAD-UHFFFAOYSA-N non-2-yne Chemical compound CCCCCCC#CC LXKRETAGISZJAD-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- MINRDQDGBLQBGD-UHFFFAOYSA-N pent-2-ynoic acid Chemical compound CCC#CC(O)=O MINRDQDGBLQBGD-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- ONCMJWSDNCJMLL-UHFFFAOYSA-N pyrazolo[1,5-c]quinazoline Chemical class C12=CC=CC=C2N=CN2C1=CC=N2 ONCMJWSDNCJMLL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/702,364 US4076818A (en) | 1976-07-02 | 1976-07-02 | Pyrazolo [1,5-C]quinazoline derivatives and related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL199270A1 PL199270A1 (pl) | 1978-09-11 |
| PL106659B1 true PL106659B1 (pl) | 1980-01-31 |
Family
ID=24820927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977199270A PL106659B1 (pl) | 1976-07-02 | 1977-06-30 | Sposob wytwarzania nowych pochodnych pirazolo/1,5-c/chinazoliny |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4076818A (enExample) |
| JP (1) | JPS5312894A (enExample) |
| AT (1) | AT361487B (enExample) |
| AU (1) | AU512177B2 (enExample) |
| BE (1) | BE856386A (enExample) |
| CA (1) | CA1097347A (enExample) |
| DE (1) | DE2726389A1 (enExample) |
| FR (1) | FR2356650A1 (enExample) |
| GB (1) | GB1585681A (enExample) |
| HU (1) | HU173531B (enExample) |
| NL (1) | NL7707086A (enExample) |
| PH (1) | PH12768A (enExample) |
| PL (1) | PL106659B1 (enExample) |
| SU (1) | SU730306A3 (enExample) |
| ZA (1) | ZA773319B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128644A (en) * | 1977-07-29 | 1978-12-05 | E. R. Squibb & Sons, Inc. | Pyrazolo(1,5-c)quinazoline derivatives and related compounds |
| US4282226A (en) * | 1978-04-26 | 1981-08-04 | E. R. Squibb & Sons, Inc. | Thioxopyrazolo[1,5-c]quinazoline derivatives, anti-allergic compositions and methods for treating allergic conditions by parenteral administration, aerosol or insufflation |
| CA1111033A (en) * | 1978-04-26 | 1981-10-20 | Berthold R. Vogt | Thioxopyrazolo[1,5-c]quinazoline derivatives and related compounds |
| US4198412A (en) * | 1978-12-13 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Pyrazolo [1,5-C] quinazoline derivatives and their use in treating allergic conditions |
| US4239896A (en) * | 1978-12-13 | 1980-12-16 | E. R. Squibb & Sons, Inc. | 5-(Optionally substituted 2-aminophenyl)-1H-pyrazole-3-methanol |
| HU178523B (en) * | 1979-05-18 | 1982-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing new pyrazolo-quinazoline derivatives |
| US4312870A (en) * | 1979-06-21 | 1982-01-26 | Ciba-Geigy Corporation | Pyrazoloquinolines |
| US4252945A (en) * | 1979-07-11 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Process for preparing pyrazolo[1,5-c]-quinazoline derivatives and novel intermediates |
| US4307099A (en) * | 1980-06-25 | 1981-12-22 | E. R. Squibb & Sons, Inc. | Reaction products of pyrazolo[1,5-c]quinazoline derivatives and proline derivatives and methods for reducing blood pressure while inhibiting allergic reactions with them |
| US4459298A (en) * | 1982-09-28 | 1984-07-10 | Ciba-Geigy Corporation | Method of suppressing appetite |
| US4713383A (en) * | 1984-10-01 | 1987-12-15 | Ciba-Geigy Corporation | Triazoloquinazoline compounds, and their methods of preparation, pharmaceutical compositions, and uses |
| US4831013A (en) * | 1986-03-20 | 1989-05-16 | Ciba-Geigy Corporation | 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111505B (de) * | 1960-02-11 | 1961-07-20 | Agfa Ag | Verfahren zur Herstellung von farbigen photographischen Aufsichts- oder Durchsichtsbildern nach dem Farbentwicklungsverfahren |
| US3313815A (en) * | 1964-05-04 | 1967-04-11 | Sterling Drug Inc | 8-chloropyrazolo-[1, 5-c]quinazoline derivatives and methods of preparing same |
| US3531482A (en) * | 1966-10-13 | 1970-09-29 | Sandoz Ag | Pyrazolo(1,5-c)quinazolines |
| DE2058501A1 (de) * | 1970-11-27 | 1972-05-31 | Bayer Ag | Verfahren zur Herstellung von neuen N-verbrueckten bicyclischen Heteroaromaten |
| JPS50116498A (enExample) * | 1974-02-27 | 1975-09-11 | ||
| US3903106A (en) * | 1974-04-12 | 1975-09-02 | Lilly Co Eli | Pyrazole-3-carboxylic acids |
| US3890324A (en) * | 1974-04-12 | 1975-06-17 | Lilly Co Eli | 1h-pyrazolo(4,3-)quinol-4(5h)-one-3-carboxylic acids |
| US3897434A (en) * | 1974-04-12 | 1975-07-29 | Lilly Co Eli | Pyrazolo{8 1,5-c{9 quinazolin-5(6H)-ones |
| US3895027A (en) * | 1974-04-12 | 1975-07-15 | Lilly Co Eli | Process for preparing pyrazole-3-carboxylic acids |
| US3899508A (en) * | 1974-04-12 | 1975-08-12 | Lilly Co Eli | 5-(2-Aminophenyl)pyrazole-3-carboxylic acids and esters thereof |
-
1976
- 1976-07-02 US US05/702,364 patent/US4076818A/en not_active Expired - Lifetime
-
1977
- 1977-03-17 US US05/778,397 patent/US4112096A/en not_active Expired - Lifetime
- 1977-06-02 ZA ZA00773319A patent/ZA773319B/xx unknown
- 1977-06-03 CA CA279,853A patent/CA1097347A/en not_active Expired
- 1977-06-03 GB GB23732/77A patent/GB1585681A/en not_active Expired
- 1977-06-03 AU AU25830/77A patent/AU512177B2/en not_active Expired
- 1977-06-09 PH PH19862A patent/PH12768A/en unknown
- 1977-06-10 DE DE19772726389 patent/DE2726389A1/de not_active Withdrawn
- 1977-06-15 AT AT424077A patent/AT361487B/de not_active IP Right Cessation
- 1977-06-27 NL NL7707086A patent/NL7707086A/xx not_active Application Discontinuation
- 1977-06-30 PL PL1977199270A patent/PL106659B1/pl unknown
- 1977-06-30 FR FR7720120A patent/FR2356650A1/fr active Granted
- 1977-06-30 HU HU77SU949A patent/HU173531B/hu unknown
- 1977-07-01 BE BE179013A patent/BE856386A/xx unknown
- 1977-07-01 SU SU772499601A patent/SU730306A3/ru active
- 1977-07-01 JP JP7943877A patent/JPS5312894A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2583077A (en) | 1978-12-07 |
| AT361487B (de) | 1981-03-10 |
| SU730306A3 (ru) | 1980-04-25 |
| JPS5312894A (en) | 1978-02-04 |
| FR2356650A1 (fr) | 1978-01-27 |
| NL7707086A (nl) | 1978-01-04 |
| PL199270A1 (pl) | 1978-09-11 |
| US4076818A (en) | 1978-02-28 |
| ZA773319B (en) | 1978-04-26 |
| ATA424077A (de) | 1980-08-15 |
| AU512177B2 (en) | 1980-09-25 |
| CA1097347A (en) | 1981-03-10 |
| FR2356650B1 (enExample) | 1981-08-28 |
| PH12768A (en) | 1979-08-17 |
| US4112096A (en) | 1978-09-05 |
| GB1585681A (en) | 1981-03-11 |
| HU173531B (en) | 1979-06-28 |
| BE856386A (fr) | 1978-01-02 |
| DE2726389A1 (de) | 1978-01-12 |
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