CA1095907A - Meso-ionic didehydro derivatives of 1,7-dehydro-1- substituted -3h-pyrazolo [4,3-e]-1,2,4-triazolo [4,3-c]-pyrimidine-3-thiones and 3-ones - Google Patents
Meso-ionic didehydro derivatives of 1,7-dehydro-1- substituted -3h-pyrazolo [4,3-e]-1,2,4-triazolo [4,3-c]-pyrimidine-3-thiones and 3-onesInfo
- Publication number
- CA1095907A CA1095907A CA309,665A CA309665A CA1095907A CA 1095907 A CA1095907 A CA 1095907A CA 309665 A CA309665 A CA 309665A CA 1095907 A CA1095907 A CA 1095907A
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- hydrogen
- methyl
- pyrazolo
- pyrimidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 239000011593 sulfur Substances 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- -1 1,7-dihydro-1-substituted-3H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidine-3-thione Chemical class 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052760 oxygen Chemical group 0.000 claims abstract description 14
- 239000001301 oxygen Chemical group 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- AMZCQXCAQVKYKZ-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(C(C)C)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(C(C)C)NC(=S)N21 AMZCQXCAQVKYKZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- DCTBMFDEKIMGLY-UHFFFAOYSA-N 1-methyl-1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Chemical compound CN(N)C1=NC=NC2=C1C=NN2C DCTBMFDEKIMGLY-UHFFFAOYSA-N 0.000 description 3
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 3
- AVFLNALVPBLGEV-UHFFFAOYSA-N 4-chloro-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C2N(C)N=CC2=C1Cl AVFLNALVPBLGEV-UHFFFAOYSA-N 0.000 description 3
- MMCGFABWPRDLAG-UHFFFAOYSA-N 5-(ethoxymethylideneamino)-1-methylpyrazole-4-carboxylic acid Chemical compound CCOC=NC1=C(C(O)=O)C=NN1C MMCGFABWPRDLAG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- SISQSWFOHNJVLP-UHFFFAOYSA-N 4-chloro-3-propan-2-yl-2h-pyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C(Cl)C2=C(C(C)C)NN=C21 SISQSWFOHNJVLP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- MEUSJJFWVKBUFP-UHFFFAOYSA-N ethyl 5-amino-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1N MEUSJJFWVKBUFP-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical group CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RVYSDXZMMQWFRL-UHFFFAOYSA-N 1-butyl-1-(1-methylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazine Chemical compound CCCCN(N)C1=NC=NC2=C1C=NN2C RVYSDXZMMQWFRL-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- VMXWGNGBYAOJAN-UHFFFAOYSA-N 3,4,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,7,11-tetraene-5-thione Chemical class N1=CN2C(S)=NN=C2C2=C1NN=C2 VMXWGNGBYAOJAN-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- AQBZXTCHSLIYRC-UHFFFAOYSA-N 5-(ethoxymethylideneamino)-1-propan-2-ylpyrazole-4-carboxylic acid Chemical compound CCOC=NC1=C(C(O)=O)C=NN1C(C)C AQBZXTCHSLIYRC-UHFFFAOYSA-N 0.000 description 1
- OSUQULRSOJLDFU-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(C)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(C)NC(=S)N21 OSUQULRSOJLDFU-UHFFFAOYSA-N 0.000 description 1
- AUBRWJZCZQAWIQ-UHFFFAOYSA-N C1N=C2N(C)N=CC2=C2N(CCCC)NC(=S)N21 Chemical compound C1N=C2N(C)N=CC2=C2N(CCCC)NC(=S)N21 AUBRWJZCZQAWIQ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical group CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- CDJQIJFWTUEUFF-UHFFFAOYSA-N chembl1401275 Chemical compound N1=CNC(=O)C2=C1N(C)N=C2 CDJQIJFWTUEUFF-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960005419 nitrogen Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/38—Nitrogen atoms
-
- 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]
-
- 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
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/833,103 US4124764A (en) | 1976-04-21 | 1977-09-13 | Meso-ionic didehydro derivatives of 1,7-dehydro-1-substituted-3H-pyrazolo[4,]-1,2,4-triazolo[4,3-c]pyrimidine-3-thiones and 3-ones |
| US833,103 | 1977-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095907A true CA1095907A (en) | 1981-02-17 |
Family
ID=25263436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,665A Expired CA1095907A (en) | 1977-09-13 | 1978-08-18 | Meso-ionic didehydro derivatives of 1,7-dehydro-1- substituted -3h-pyrazolo [4,3-e]-1,2,4-triazolo [4,3-c]-pyrimidine-3-thiones and 3-ones |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5452098A (no) |
| AU (1) | AU3914178A (no) |
| BE (1) | BE870456A (no) |
| CA (1) | CA1095907A (no) |
| DE (1) | DE2838029A1 (no) |
| DK (1) | DK402178A (no) |
| FR (1) | FR2402658A1 (no) |
| GB (1) | GB2004278B (no) |
| HU (1) | HU176023B (no) |
| IT (1) | IT1099031B (no) |
| NL (1) | NL7809035A (no) |
| NO (1) | NO783086L (no) |
| SE (1) | SE7809601L (no) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053474A (en) * | 1976-04-21 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine |
-
1978
- 1978-08-18 CA CA309,665A patent/CA1095907A/en not_active Expired
- 1978-08-22 AU AU39141/78A patent/AU3914178A/en active Pending
- 1978-08-31 DE DE19782838029 patent/DE2838029A1/de not_active Withdrawn
- 1978-09-04 NL NL7809035A patent/NL7809035A/xx not_active Application Discontinuation
- 1978-09-11 HU HU78SU991A patent/HU176023B/hu unknown
- 1978-09-11 FR FR7826046A patent/FR2402658A1/fr not_active Withdrawn
- 1978-09-12 IT IT27559/78A patent/IT1099031B/it active
- 1978-09-12 NO NO783086A patent/NO783086L/no unknown
- 1978-09-12 GB GB7836516A patent/GB2004278B/en not_active Expired
- 1978-09-12 SE SE7809601A patent/SE7809601L/xx unknown
- 1978-09-12 DK DK402178A patent/DK402178A/da unknown
- 1978-09-13 JP JP11321978A patent/JPS5452098A/ja active Pending
- 1978-09-13 BE BE190466A patent/BE870456A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2004278B (en) | 1982-01-13 |
| DE2838029A1 (de) | 1979-03-22 |
| NL7809035A (nl) | 1979-03-15 |
| DK402178A (da) | 1979-03-14 |
| JPS5452098A (en) | 1979-04-24 |
| BE870456A (fr) | 1979-03-13 |
| AU3914178A (en) | 1980-02-28 |
| IT7827559A0 (it) | 1978-09-12 |
| HU176023B (en) | 1980-11-28 |
| IT1099031B (it) | 1985-09-18 |
| SE7809601L (sv) | 1979-03-14 |
| GB2004278A (en) | 1979-03-28 |
| FR2402658A1 (fr) | 1979-04-06 |
| NO783086L (no) | 1979-03-14 |
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