PL82369B1 - Amino-pyrazolopyrimidines and processes for their production[gb1396302a] - Google Patents
Amino-pyrazolopyrimidines and processes for their production[gb1396302a] Download PDFInfo
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- PL82369B1 PL82369B1 PL1972154974A PL15497472A PL82369B1 PL 82369 B1 PL82369 B1 PL 82369B1 PL 1972154974 A PL1972154974 A PL 1972154974A PL 15497472 A PL15497472 A PL 15497472A PL 82369 B1 PL82369 B1 PL 82369B1
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- Prior art keywords
- formula
- compound
- methyl
- lower alkyl
- general formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 2
- AVFCGLFLHBWEET-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-3-amine Chemical class N1=CN=C2C(N)=NNC2=C1 AVFCGLFLHBWEET-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- -1 polymethylene chain Polymers 0.000 claims abstract description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims 2
- 241000353790 Doru Species 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910003460 diamond Inorganic materials 0.000 claims 1
- 239000010432 diamond Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 241001465754 Metazoa Species 0.000 abstract description 4
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- 150000000183 1,3-benzoxazoles Chemical class 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004305 biphenyl Substances 0.000 abstract description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 abstract description 2
- 229960002597 sulfamerazine Drugs 0.000 abstract description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 abstract description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 abstract 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical class SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
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- 229960000654 sulfafurazole Drugs 0.000 abstract 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 14
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
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- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 229960000583 acetic acid Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000004954 trialkylamino group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Control Of Steam Boilers And Waste-Gas Boilers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1149271 | 1971-04-27 | ||
| GB478872*[A GB1396302A (en) | 1971-04-27 | 1972-02-02 | Amino-pyrazolopyrimidines and processes for their production |
| GB1002172 | 1972-03-03 | ||
| GB1002272 | 1972-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82369B1 true PL82369B1 (en) | 1975-10-31 |
Family
ID=27447397
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972154974A PL82369B1 (en) | 1971-04-27 | 1972-04-25 | Amino-pyrazolopyrimidines and processes for their production[gb1396302a] |
| PL1972175239A PL84544B1 (en) | 1971-04-27 | 1972-04-25 | Amino-pyrazolopyrimidines and processes for their production[gb1396302a] |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972175239A PL84544B1 (en) | 1971-04-27 | 1972-04-25 | Amino-pyrazolopyrimidines and processes for their production[gb1396302a] |
Country Status (20)
| Country | Link |
|---|---|
| AR (1) | AR205429A1 (OSRAM) |
| AT (1) | AT314527B (OSRAM) |
| AU (1) | AU471025B2 (OSRAM) |
| BE (1) | BE782658A (OSRAM) |
| CA (1) | CA995668A (OSRAM) |
| CH (1) | CH568320A5 (OSRAM) |
| DD (1) | DD98288A5 (OSRAM) |
| DE (1) | DE2218717A1 (OSRAM) |
| DK (1) | DK138896B (OSRAM) |
| FI (1) | FI54122C (OSRAM) |
| FR (1) | FR2134540B1 (OSRAM) |
| GB (1) | GB1396302A (OSRAM) |
| HU (1) | HU168494B (OSRAM) |
| IE (1) | IE36312B1 (OSRAM) |
| IL (1) | IL39247A (OSRAM) |
| NL (1) | NL7205668A (OSRAM) |
| NO (1) | NO129576B (OSRAM) |
| PL (2) | PL82369B1 (OSRAM) |
| SE (1) | SE395275B (OSRAM) |
| SU (1) | SU493069A3 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204665A1 (es) * | 1974-05-13 | 1976-02-20 | Lilly Co Eli | Procedimiento para preparar compuestos de 3-(5-nitroimidazol-2-il)pirazolo(3,4d)pirimidina |
| GB0610242D0 (en) * | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
-
1972
- 1972-01-01 AR AR241693A patent/AR205429A1/es active
- 1972-02-02 GB GB478872*[A patent/GB1396302A/en not_active Expired
- 1972-04-17 NO NO01324/72A patent/NO129576B/no unknown
- 1972-04-18 IL IL39247A patent/IL39247A/xx unknown
- 1972-04-18 FI FI1086/72A patent/FI54122C/fi active
- 1972-04-18 DE DE19722218717 patent/DE2218717A1/de active Pending
- 1972-04-19 SE SE7205085A patent/SE395275B/xx unknown
- 1972-04-20 IE IE523/72A patent/IE36312B1/xx unknown
- 1972-04-25 CH CH610372A patent/CH568320A5/xx not_active IP Right Cessation
- 1972-04-25 PL PL1972154974A patent/PL82369B1/pl unknown
- 1972-04-25 PL PL1972175239A patent/PL84544B1/pl unknown
- 1972-04-26 BE BE782658A patent/BE782658A/xx unknown
- 1972-04-26 FR FR7214835A patent/FR2134540B1/fr not_active Expired
- 1972-04-26 SU SU1779675A patent/SU493069A3/ru active
- 1972-04-26 CA CA140,603A patent/CA995668A/en not_active Expired
- 1972-04-26 DD DD162588A patent/DD98288A5/xx unknown
- 1972-04-26 DK DK207672AA patent/DK138896B/da unknown
- 1972-04-26 NL NL7205668A patent/NL7205668A/xx not_active Application Discontinuation
- 1972-04-26 AU AU41539/72A patent/AU471025B2/en not_active Expired
- 1972-04-26 AT AT368072A patent/AT314527B/de not_active IP Right Cessation
- 1972-04-27 HU HUCI1229A patent/HU168494B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO129576B (OSRAM) | 1974-04-29 |
| IE36312B1 (en) | 1976-10-13 |
| AU471025B2 (en) | 1976-04-08 |
| DD98288A5 (OSRAM) | 1973-06-12 |
| SE395275B (sv) | 1977-08-08 |
| BE782658A (fr) | 1972-10-26 |
| HU168494B (OSRAM) | 1976-05-28 |
| DE2218717A1 (de) | 1972-11-16 |
| AU4153972A (en) | 1973-11-01 |
| AT314527B (de) | 1974-04-10 |
| IL39247A0 (en) | 1972-06-28 |
| DK138896C (OSRAM) | 1979-04-30 |
| CH568320A5 (OSRAM) | 1975-10-31 |
| DK138896B (da) | 1978-11-13 |
| AR205429A1 (es) | 1976-05-07 |
| GB1396302A (en) | 1975-06-04 |
| FR2134540A1 (OSRAM) | 1972-12-08 |
| PL84544B1 (en) | 1976-04-30 |
| FI54122B (fi) | 1978-06-30 |
| FR2134540B1 (OSRAM) | 1975-12-26 |
| CA995668A (en) | 1976-08-24 |
| SU493069A3 (ru) | 1975-11-25 |
| NL7205668A (OSRAM) | 1972-10-31 |
| IL39247A (en) | 1975-07-28 |
| FI54122C (fi) | 1978-10-10 |
| IE36312L (en) | 1972-10-27 |
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