DE2236987A1 - Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine und verfahren zu ihrer herstellung - Google Patents
Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine und verfahren zu ihrer herstellungInfo
- Publication number
- DE2236987A1 DE2236987A1 DE2236987A DE2236987A DE2236987A1 DE 2236987 A1 DE2236987 A1 DE 2236987A1 DE 2236987 A DE2236987 A DE 2236987A DE 2236987 A DE2236987 A DE 2236987A DE 2236987 A1 DE2236987 A1 DE 2236987A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- product
- sodium
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 108010093894 Xanthine oxidase Proteins 0.000 claims description 8
- 102100033220 Xanthine oxidase Human genes 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- BUEFDJQUUGMUJO-UHFFFAOYSA-N 1h-pyrazolo[1,5-a]pyrimidin-7-one Chemical compound O=C1C=CN=C2C=CNN12 BUEFDJQUUGMUJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- SLHCRNWCKCTZMF-UHFFFAOYSA-N chembl3276835 Chemical compound N1=C(O)C=C(O)N2N=CC=C21 SLHCRNWCKCTZMF-UHFFFAOYSA-N 0.000 claims 2
- UMOILRYDPQMJET-UHFFFAOYSA-N chembl3276839 Chemical compound C=12N=C(O)C=C(O)N2N=CC=1C1=CC=CC=C1 UMOILRYDPQMJET-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000047 product Substances 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 159000000000 sodium salts Chemical class 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 19
- 238000001914 filtration Methods 0.000 description 18
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 16
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 15
- 229940116269 uric acid Drugs 0.000 description 15
- 229960003459 allopurinol Drugs 0.000 description 14
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 13
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 13
- 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 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 10
- 238000001226 reprecipitation Methods 0.000 description 9
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 230000020477 pH reduction Effects 0.000 description 7
- 229940075420 xanthine Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 201000005569 Gout Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003217 pyrazoles Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- -1 for example Chemical group 0.000 description 4
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VAKJBMPZWKCBAW-UHFFFAOYSA-N 4-(3-methylphenyl)-1h-pyrazol-5-amine Chemical compound CC1=CC=CC(C2=C(NN=C2)N)=C1 VAKJBMPZWKCBAW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- QEHKQNYBBLCFIJ-UHFFFAOYSA-N 4-phenyl-1h-pyrazol-5-amine Chemical compound NC1=NNC=C1C1=CC=CC=C1 QEHKQNYBBLCFIJ-UHFFFAOYSA-N 0.000 description 2
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- LQOZGZQLNDEHLB-UHFFFAOYSA-N 3-phenyl-1h-pyrazolo[1,5-a]pyrimidin-7-one Chemical compound C=1NN2C(=O)C=CN=C2C=1C1=CC=CC=C1 LQOZGZQLNDEHLB-UHFFFAOYSA-N 0.000 description 1
- CTZUARZJFPNNTM-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(CC=2C=C3OCOC3=CC=2)=C1N CTZUARZJFPNNTM-UHFFFAOYSA-N 0.000 description 1
- ABKUXQSVMWMABM-UHFFFAOYSA-N 4-(4-bromophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(Br)=CC=2)=C1N ABKUXQSVMWMABM-UHFFFAOYSA-N 0.000 description 1
- VNDBRCBZFIAMRE-UHFFFAOYSA-N 4-(4-methylphenyl)-1h-pyrazol-5-amine Chemical compound C1=CC(C)=CC=C1C1=C(N)NN=C1 VNDBRCBZFIAMRE-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 201000001431 Hyperuricemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- MMOXBMOAPCBXPP-UHFFFAOYSA-N chembl422694 Chemical compound CC1=CC=CC(C2=C3N=CC=C(O)N3N=C2)=C1 MMOXBMOAPCBXPP-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- SYFFHRPDTQNMQB-UHFFFAOYSA-N ethyl 3-oxopropanoate Chemical compound CCOC(=O)CC=O SYFFHRPDTQNMQB-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17219571A | 1971-08-16 | 1971-08-16 | |
| US261103A US3920652A (en) | 1971-08-16 | 1972-06-08 | Aromatic substituted pyrazola {8 1,5a{9 {0 pyrimidine compounds useful as xanthine oxidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2236987A1 true DE2236987A1 (de) | 1973-03-01 |
Family
ID=26867834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236987A Pending DE2236987A1 (de) | 1971-08-16 | 1972-07-27 | Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine und verfahren zu ihrer herstellung |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3920652A (enExample) |
| JP (1) | JPS4834899A (enExample) |
| AR (1) | AR193536A1 (enExample) |
| AT (1) | AT330780B (enExample) |
| BE (1) | BE786611A (enExample) |
| BG (1) | BG19806A3 (enExample) |
| DD (1) | DD99581A5 (enExample) |
| DE (1) | DE2236987A1 (enExample) |
| ES (1) | ES405663A1 (enExample) |
| FR (1) | FR2150771B1 (enExample) |
| GB (1) | GB1359563A (enExample) |
| HU (1) | HU167466B (enExample) |
| IE (1) | IE36629B1 (enExample) |
| IL (1) | IL39988A0 (enExample) |
| LU (1) | LU65892A1 (enExample) |
| MC (1) | MC937A1 (enExample) |
| NL (1) | NL7211011A (enExample) |
| RO (1) | RO63871A (enExample) |
| SU (1) | SU522800A3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025819A1 (en) * | 1979-07-09 | 1981-04-01 | American Cyanamid Company | Substituted pyrazolo (1,5-a) pyrimidines, and their preparation |
| EP0795555A4 (en) * | 1995-09-28 | 1998-01-07 | Otsuka Pharma Co Ltd | ANALGESICS |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093617A (en) * | 1974-11-12 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 3,5,7-Trisubstituted pyrazolo[1,5-a]pyrimidines |
| US4048184A (en) * | 1976-11-15 | 1977-09-13 | E. R. Squibb & Sons, Inc. | 6-Phenyl-2H-pyrazolo[3,4-b]pyridines |
| AU557300B2 (en) * | 1982-03-16 | 1986-12-18 | Farmitalia Carlo Erba S.P.A. | Substituted 1h-pyrazolo(1,5-alpha)pyrimidines and processes for their preparation |
| ZA831407B (en) * | 1982-03-25 | 1983-11-30 | Erba Farmitalia | Substituted ethenyl derivatives of 1h-pyrazolo(1,5-a)pyrimidine and process for their preparation |
| WO1992006096A1 (fr) * | 1990-10-09 | 1992-04-16 | Otsuka Pharmaceutical Co., Ltd. | Derive de pyrimidine, production de ce derive et inhibiteur d'androgenes |
| AU667575B2 (en) * | 1992-10-20 | 1996-03-28 | Otsuka Pharmaceutical Co., Ltd. | Condensed pyrazole derivatives, method of manufacturing the same, and androgen inhibitor |
| US6664261B2 (en) * | 1996-02-07 | 2003-12-16 | Neurocrine Biosciences, Inc. | Pyrazolopyrimidines as CRF receptor antagonists |
| HU228962B1 (en) * | 1996-07-24 | 2013-07-29 | Bristol Myers Squibb Pharma Co | Azolo triazines, pharmaceutical compositions containing them and use of the compounds |
| US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
| US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| US6235741B1 (en) * | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| EP1044002A4 (en) | 1997-11-07 | 2003-05-02 | Univ Johns Hopkins | METHODS FOR THE TREATMENT OF HEART CONTRACTILITY |
| US6380203B1 (en) * | 1998-01-14 | 2002-04-30 | Merck & Co., Inc. | Angiogenesis inhibitors |
| AU4331500A (en) | 1999-04-06 | 2000-10-23 | Du Pont Pharmaceuticals Company | Pyrazolotriazines as crf antagonists |
| WO2000059908A2 (en) | 1999-04-06 | 2000-10-12 | Du Pont Pharmaceuticals Company | Pyrazolopyrimidines as crf antagonists |
| US6630476B2 (en) | 2000-07-07 | 2003-10-07 | Bristol-Myers Squibb Pharma Company | Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists |
| WO2015186117A1 (en) | 2014-06-06 | 2015-12-10 | Siemens Medical Solutions Usa, Inc. | Gamma camera dead time determination in real time using long lived radioisotopes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048587A (en) * | 1960-10-17 | 1962-08-07 | Ortho Pharma Corp | 2-alkylamino-4-aminopyrimidine |
| US3296268A (en) * | 1965-10-19 | 1967-01-03 | Searle & Co | 3-cyanoethyl-2-oxo-5-phenyl [1, 5-a] pyrimidines |
-
0
- BE BE786611D patent/BE786611A/xx unknown
-
1972
- 1972-06-08 US US261103A patent/US3920652A/en not_active Expired - Lifetime
- 1972-07-25 IL IL39988A patent/IL39988A0/xx unknown
- 1972-07-27 DE DE2236987A patent/DE2236987A1/de active Pending
- 1972-08-02 MC MC1005A patent/MC937A1/fr unknown
- 1972-08-04 AT AT677372A patent/AT330780B/de not_active IP Right Cessation
- 1972-08-07 GB GB3680472A patent/GB1359563A/en not_active Expired
- 1972-08-08 AR AR243489A patent/AR193536A1/es active
- 1972-08-08 ES ES405663A patent/ES405663A1/es not_active Expired
- 1972-08-08 IE IE1107/72A patent/IE36629B1/xx unknown
- 1972-08-11 FR FR7229107A patent/FR2150771B1/fr not_active Expired
- 1972-08-11 LU LU65892A patent/LU65892A1/xx unknown
- 1972-08-11 NL NL7211011A patent/NL7211011A/xx unknown
- 1972-08-14 DD DD165054A patent/DD99581A5/xx unknown
- 1972-08-14 BG BG021195A patent/BG19806A3/xx unknown
- 1972-08-15 SU SU1821375A patent/SU522800A3/ru active
- 1972-08-15 HU HUIE526A patent/HU167466B/hu unknown
- 1972-08-16 JP JP47082059A patent/JPS4834899A/ja active Pending
- 1972-08-16 RO RO7200071971A patent/RO63871A/ro unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025819A1 (en) * | 1979-07-09 | 1981-04-01 | American Cyanamid Company | Substituted pyrazolo (1,5-a) pyrimidines, and their preparation |
| EP0795555A4 (en) * | 1995-09-28 | 1998-01-07 | Otsuka Pharma Co Ltd | ANALGESICS |
| US5843951A (en) * | 1995-09-28 | 1998-12-01 | Otsuka Pharmaceutical Factory Inc. | Analgesic composition of pyrazolo(1,5-A) pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| BG19806A3 (bg) | 1975-10-10 |
| US3920652A (en) | 1975-11-18 |
| SU522800A3 (ru) | 1976-07-25 |
| GB1359563A (en) | 1974-07-10 |
| RO63871A (fr) | 1979-01-15 |
| BE786611A (fr) | 1973-01-22 |
| DD99581A5 (enExample) | 1973-08-12 |
| AT330780B (de) | 1976-07-26 |
| LU65892A1 (enExample) | 1973-01-15 |
| FR2150771B1 (enExample) | 1976-05-21 |
| HU167466B (enExample) | 1975-10-28 |
| MC937A1 (fr) | 1973-08-10 |
| NL7211011A (enExample) | 1973-02-20 |
| FR2150771A1 (enExample) | 1973-04-13 |
| AR193536A1 (es) | 1973-04-30 |
| JPS4834899A (enExample) | 1973-05-22 |
| IE36629L (en) | 1973-02-16 |
| ES405663A1 (es) | 1976-01-16 |
| IL39988A0 (en) | 1972-09-28 |
| IE36629B1 (en) | 1977-01-19 |
| ATA677372A (de) | 1975-10-15 |
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