ZA200205838B - Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases. - Google Patents
Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases. Download PDFInfo
- Publication number
- ZA200205838B ZA200205838B ZA200205838A ZA200205838A ZA200205838B ZA 200205838 B ZA200205838 B ZA 200205838B ZA 200205838 A ZA200205838 A ZA 200205838A ZA 200205838 A ZA200205838 A ZA 200205838A ZA 200205838 B ZA200205838 B ZA 200205838B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrrol
- methyl
- group
- ylidene
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 405
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 72
- 201000011510 cancer Diseases 0.000 title claims abstract description 71
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 33
- 201000010099 disease Diseases 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims description 179
- 238000000034 method Methods 0.000 title claims description 47
- 230000003612 virological effect Effects 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 143
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 492
- 125000000217 alkyl group Chemical group 0.000 claims description 444
- 229910052799 carbon Inorganic materials 0.000 claims description 444
- -1 (1- methyl)butyl Chemical group 0.000 claims description 285
- 125000006414 CCl Chemical group ClC* 0.000 claims description 56
- 239000003937 drug carrier Substances 0.000 claims description 52
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 47
- 210000004027 cell Anatomy 0.000 claims description 46
- 238000011282 treatment Methods 0.000 claims description 43
- 230000002401 inhibitory effect Effects 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 230000002265 prevention Effects 0.000 claims description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
- 241000700605 Viruses Species 0.000 claims description 34
- 125000001475 halogen functional group Chemical group 0.000 claims description 33
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 210000005170 neoplastic cell Anatomy 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 31
- DSHIIBUGOWQFSO-LICLKQGHSA-N Cycloprodigiosin Natural products COC1=CC(=N\C1=C\c1[nH]c(C)c2CCCC(C)c12)c1ccc[nH]1 DSHIIBUGOWQFSO-LICLKQGHSA-N 0.000 claims description 29
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 27
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 26
- XEPVVPTUOMXJRW-SFHVURJKSA-N metacycloprodiginine Natural products CC[C@H]1CCCCCCCCc2cc1c(C=C3N=C(C=C3OC)c4ccc[nH]4)[nH]2 XEPVVPTUOMXJRW-SFHVURJKSA-N 0.000 claims description 25
- XEPVVPTUOMXJRW-JLPGSUDCSA-N metacycloprodigiosin Chemical compound CCC1CCCCCCCCC(N2)=CC1=C2\C=C(C(=C1)OC)/N=C1C1=CC=CN1 XEPVVPTUOMXJRW-JLPGSUDCSA-N 0.000 claims description 25
- 208000036142 Viral infection Diseases 0.000 claims description 24
- XEPVVPTUOMXJRW-UHFFFAOYSA-N metacycloprodigiosin Natural products CCC1CCCCCCCCc2cc1c(C=C3/N=C(C=C3OC)c4ccc[nH]4)[nH]2 XEPVVPTUOMXJRW-UHFFFAOYSA-N 0.000 claims description 24
- 230000009385 viral infection Effects 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 230000010076 replication Effects 0.000 claims description 21
- TXFXBRICRNFFRR-JLPGSUDCSA-N chembl1812867 Chemical compound CCCCC1CCCCCCC(N2)=CC1=C2\C=C(C(=C1)OC)/N=C1C1=CC=CN1 TXFXBRICRNFFRR-JLPGSUDCSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- HCOLPNRPCMFHOH-UHFFFAOYSA-N Prodigiosin Natural products CCCCCC1C=C(C=C/2N=C(C=C2OC)c3ccc[nH]3)N=C1C HCOLPNRPCMFHOH-UHFFFAOYSA-N 0.000 claims description 15
- HIYSWASSDOXZLC-HKOYGPOVSA-N undecylprodigiosin Chemical compound N1C(CCCCCCCCCCC)=CC=C1\C=C\1C(OC)=CC(C=2NC=CC=2)=N/1 HIYSWASSDOXZLC-HKOYGPOVSA-N 0.000 claims description 15
- TWFGRJUTAULJPZ-USZBIXTISA-N prodigiosin Chemical compound N1=C(C)C(CCCCC)=C\C1=C/C1=NC(C=2[N]C=CC=2)=C[C]1OC TWFGRJUTAULJPZ-USZBIXTISA-N 0.000 claims description 14
- ZFWNFDJEWPSCJW-UHFFFAOYSA-N Nonylprodigiosin Natural products CCCCCCCCCc1c[nH]c(C=C2/N=C(C=C2OC)c3ccc[nH]3)c1 ZFWNFDJEWPSCJW-UHFFFAOYSA-N 0.000 claims description 12
- HIYSWASSDOXZLC-UHFFFAOYSA-N Undecylprodigiosin Natural products CCCCCCCCCCCc1ccc(C=C2N=C(C=C2OC)c2ccc[nH]2)[nH]1 HIYSWASSDOXZLC-UHFFFAOYSA-N 0.000 claims description 12
- SXTCZAFEGDEUIB-PGMHBOJBSA-N cyclononylprodiginine Chemical compound C1CCCCCCCCN2C=CC=C2C(C=C2OC)=N\C2=C/C2=CC=C1N2 SXTCZAFEGDEUIB-PGMHBOJBSA-N 0.000 claims description 12
- BFSYHQVSNYPCNA-JLPGSUDCSA-N methylcyclodecylprodiginine Chemical compound C1CCCCCCCCC(C)C(N2)=CC=C2C(C=C2OC)=N\C2=C/C2=CC=C1N2 BFSYHQVSNYPCNA-JLPGSUDCSA-N 0.000 claims description 12
- JPPBJMYDABMXAF-JCMHNJIXSA-N nonylprodigiosin Chemical compound C1CCCCCCCCC(N2)=CC=C2C(C=C2OC)=N\C2=C/C2=CC=C1N2 JPPBJMYDABMXAF-JCMHNJIXSA-N 0.000 claims description 12
- UNTPUEPVEUZJII-JLPGSUDCSA-N ethylcyclononylprodiginine Chemical compound N1C2=CC=C1C(CC)CCCCCCCCC(N1)=CC=C1\C=C/1C(OC)=CC2=N\1 UNTPUEPVEUZJII-JLPGSUDCSA-N 0.000 claims description 11
- NEVDHLOEQKTLDO-WQRHYEAKSA-N (2z)-2-[(5-methyl-4-pentyl-1h-pyrrol-2-yl)methylidene]-5-(1h-pyrrol-2-yl)-1h-pyrrol-3-one Chemical compound N1C(C)=C(CCCCC)C=C1\C=C/1C(=O)C=C(C=2NC=CC=2)N\1 NEVDHLOEQKTLDO-WQRHYEAKSA-N 0.000 claims description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- HTGIZTBAHPGBKW-UHFFFAOYSA-N Norprodigiosin Natural products CCCCCC1=CC(=C/c2[nH]c(cc2O)c3ccc[nH]3)N=C1C HTGIZTBAHPGBKW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- OSVAYRLEBVNTTC-HMAPJEAMSA-N methylcyclooctylprodiginine Chemical compound C1CCCCCCC(C)C(N2)=CC=C2C(C=C2OC)=N\C2=C/C2=CC=C1N2 OSVAYRLEBVNTTC-HMAPJEAMSA-N 0.000 claims description 8
- LLCFONQVQVCMSG-UHFFFAOYSA-N C1=C2CCCCC2=NC1=C(C(CC)CCC)C(=C(C=1)OC)NC=1C1=CC=CN1 Chemical compound C1=C2CCCCC2=NC1=C(C(CC)CCC)C(=C(C=1)OC)NC=1C1=CC=CN1 LLCFONQVQVCMSG-UHFFFAOYSA-N 0.000 claims description 7
- OQYXJYGAOZNUQI-UHFFFAOYSA-N N1C(C(C(CC)CCC)=C2N=C3CCCCC3=C2)=C(OCCC)C=C1C1=CC=CN1 Chemical compound N1C(C(C(CC)CCC)=C2N=C3CCCCC3=C2)=C(OCCC)C=C1C1=CC=CN1 OQYXJYGAOZNUQI-UHFFFAOYSA-N 0.000 claims description 7
- CCDSWDGXLHOEEL-UHFFFAOYSA-N C1=C2CCCCC2=NC1=C(C(CC)CCC)C(=C(C=1)OCC)NC=1C1=CC=CN1 Chemical compound C1=C2CCCCC2=NC1=C(C(CC)CCC)C(=C(C=1)OCC)NC=1C1=CC=CN1 CCDSWDGXLHOEEL-UHFFFAOYSA-N 0.000 claims description 6
- DSHIIBUGOWQFSO-YVLHZVERSA-N cycloprodigiosin Chemical compound N=1\C(=C/C2=C3C(C)CCCC3=C(C)N2)C(OC)=CC=1C1=CC=CN1 DSHIIBUGOWQFSO-YVLHZVERSA-N 0.000 claims 12
- HJLPJTJOEAIKSK-UHFFFAOYSA-N 2-heptyl-7-methoxy-1-methyl-3-propyl-14H,16H-prodigiosene Natural products CCCCCCCC1=C(C)NC(C=C2C(=CC(=N2)C=2NC=CC=2)OC)=C1CCC HJLPJTJOEAIKSK-UHFFFAOYSA-N 0.000 claims 8
- FVCHYKQITKARRX-UHFFFAOYSA-N 1,4-diethyl-3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-4,5,6,7-tetrahydro-2H-isoindole Chemical compound C=12C(CC)CCCC2=C(CC)NC=1C=C(C(=C1)OC)N=C1C1=CC=CN1 FVCHYKQITKARRX-UHFFFAOYSA-N 0.000 claims 6
- MCJFTHRJRNFSLM-UHFFFAOYSA-N 1-ethyl-3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-4,5,6,7-tetrahydro-2H-isoindole Chemical compound C=12CCCCC2=C(CC)NC=1C=C(C(=C1)OC)N=C1C1=CC=CN1 MCJFTHRJRNFSLM-UHFFFAOYSA-N 0.000 claims 6
- CYTZKWQJVAYGMM-UHFFFAOYSA-N 1-ethyl-3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-4-methyl-4,5,6,7-tetrahydro-2H-isoindole Chemical compound C=12C(C)CCCC2=C(CC)NC=1C=C(C(=C1)OC)N=C1C1=CC=CN1 CYTZKWQJVAYGMM-UHFFFAOYSA-N 0.000 claims 6
- YEBRAKKELQMJBC-UHFFFAOYSA-N 4-ethyl-3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-1-methyl-4,5,6,7-tetrahydro-2H-isoindole Chemical compound C=12C(CC)CCCC2=C(C)NC=1C=C(C(=C1)OC)N=C1C1=CC=CN1 YEBRAKKELQMJBC-UHFFFAOYSA-N 0.000 claims 6
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- KJAXGEUODLTJCN-UHFFFAOYSA-N N1C(C=C2N=C3CCCCC3=C2)=C(OC)C=C1C1=CC=CN1 Chemical compound N1C(C=C2N=C3CCCCC3=C2)=C(OC)C=C1C1=CC=CN1 KJAXGEUODLTJCN-UHFFFAOYSA-N 0.000 claims 6
- SJCYWCVCYATOHY-UHFFFAOYSA-N 1,4-dimethyl-3-[[5-(1-methylpyrrol-2-yl)-3-phenylmethoxypyrrol-2-ylidene]methyl]-4,5,6,7-tetrahydro-2h-isoindole Chemical compound C=12C(C)CCCC2=C(C)NC=1C=C1N=C(C=2N(C=CC=2)C)C=C1OCC1=CC=CC=C1 SJCYWCVCYATOHY-UHFFFAOYSA-N 0.000 claims 5
- WINLLQXMIJLDLM-UHFFFAOYSA-N 3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-4,5,6,7-tetrahydro-1H-indole Chemical compound N=1C(=CC=2C=3CCCCC=3NC=2)C(OC)=CC=1C1=CC=CN1 WINLLQXMIJLDLM-UHFFFAOYSA-N 0.000 claims 5
- QGOOVNUDIXEJIM-UHFFFAOYSA-N 3-[[3-methoxy-5-(1H-pyrrol-2-yl)pyrrol-2-ylidene]methyl]-5-methyl-4,5,6,7-tetrahydro-1H-indole Chemical compound N=1C(=CC=2C=3CC(C)CCC=3NC=2)C(OC)=CC=1C1=CC=CN1 QGOOVNUDIXEJIM-UHFFFAOYSA-N 0.000 claims 5
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- QEVDCWRFEOZGOP-UHFFFAOYSA-N 3-methoxy-2-[[3-methoxy-5-(1H-pyrrol-2-yl)-1H-pyrrol-2-yl]methylidene]-5-(1H-pyrrol-2-yl)pyrrole Chemical compound COC1=CC(C=2NC=CC=2)=NC1=CC(=C(C=1)OC)NC=1C1=CC=CN1 QEVDCWRFEOZGOP-UHFFFAOYSA-N 0.000 claims 3
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- 238000011275 oncology therapy Methods 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000004083 survival effect Effects 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
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/491,712 US6407244B1 (en) | 2000-01-26 | 2000-01-26 | Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200205838B true ZA200205838B (en) | 2004-03-08 |
Family
ID=23953337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200205838A ZA200205838B (en) | 2000-01-26 | 2002-07-22 | Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6407244B1 (de) |
| EP (2) | EP1431286A3 (de) |
| JP (1) | JP2003523352A (de) |
| KR (1) | KR20020072295A (de) |
| CN (1) | CN1419553A (de) |
| AT (1) | ATE269859T1 (de) |
| AU (1) | AU780647B2 (de) |
| BR (1) | BR0107912A (de) |
| CA (1) | CA2398173A1 (de) |
| CZ (1) | CZ20022604A3 (de) |
| DE (1) | DE60103978D1 (de) |
| IL (1) | IL150817A0 (de) |
| MX (1) | MXPA02007271A (de) |
| NO (1) | NO20023486L (de) |
| NZ (1) | NZ520361A (de) |
| PL (1) | PL356932A1 (de) |
| SK (1) | SK10952002A3 (de) |
| WO (1) | WO2001055131A2 (de) |
| ZA (1) | ZA200205838B (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040014987A1 (en) * | 2000-01-26 | 2004-01-22 | Gemin X Biotechnologies Inc. | Pyrrole-Type compounds, compositions, and methods for treating cancer or viral diseases |
| US6407244B1 (en) | 2000-01-26 | 2002-06-18 | Gemin X Biotechnologies Inc. | Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases |
| US7144912B2 (en) * | 2001-07-18 | 2006-12-05 | Gemin X Biotechnologies Inc. | Pyrrole-type compounds, compositions, and methods for treating cancer, treating viral diseases and causing immunosuppression |
| US20030119894A1 (en) * | 2001-07-20 | 2003-06-26 | Gemin X Biotechnologies Inc. | Methods for treatment of cancer or neoplastic disease and for inhibiting growth of cancer cells and neoplastic cells |
| WO2004002367A1 (fr) * | 2002-06-27 | 2004-01-08 | Microport Medical (Shanghai) Co., Ltd. | Stent eluant des medicaments |
| PL1644363T3 (pl) | 2003-05-30 | 2012-07-31 | Gemin X Pharmaceuticals Canada Inc | Związki triheterocykliczne, kompozycje i metody leczenia raka |
| WO2006069441A1 (en) * | 2004-12-28 | 2006-07-06 | Gemin X Biotechnologies Inc. | Dipyrrole compounds, compositions, and methods for treating cancer or viral diseases |
| CA2692977A1 (en) * | 2007-07-12 | 2009-01-15 | Tragara Pharmaceuticals, Inc. | Methods and compositions for the treatment of cancer, tumors, and tumor-related disorders |
| EP2224919A4 (de) * | 2007-11-28 | 2011-09-14 | Tragara Pharmaceuticals Inc | Verfahren und zusammensetzungen zur behandlung von krebs, tumoren und tumor-bedingten erkrankungen |
| CN103145719B (zh) * | 2013-02-27 | 2015-04-29 | 中国科学院化学研究所 | 灵菌红素衍生物的制备方法 |
| AU2015324072B2 (en) | 2014-09-29 | 2018-12-06 | The Penn State Research Foundation | A compound for anti-cancer therapy that acts by targeting GOF mutant P53 and stimulates P73 |
| US10111554B2 (en) | 2015-03-20 | 2018-10-30 | Meltz, LLC | Systems for and methods of controlled liquid food or beverage product creation |
| US10314320B2 (en) | 2015-03-20 | 2019-06-11 | Meltz, LLC | Systems for controlled liquid food or beverage product creation |
| KR101785428B1 (ko) | 2016-04-21 | 2017-10-16 | (주) 마이크로프랜드 | 반도체소자 테스트소켓 |
| KR20200126887A (ko) | 2017-04-27 | 2020-11-09 | 코메티어 인크. | 원심 추출 방법 및 이 방법을 수행하기에 적합한 장치 |
| CN109942559A (zh) * | 2019-03-08 | 2019-06-28 | 上海大学 | 呋喃二联吡咯化合物及其制备方法 |
| US11724849B2 (en) | 2019-06-07 | 2023-08-15 | Cometeer, Inc. | Packaging and method for single serve beverage product |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4266028A (en) * | 1979-02-21 | 1981-05-05 | Kirin Beer Kabushiki Kaisha | Process for preparation of prodigiosin |
| JPS55162768A (en) * | 1979-06-06 | 1980-12-18 | Kirin Brewery Co Ltd | Carcinostatic |
| JPS6134403A (ja) | 1984-07-26 | 1986-02-18 | Nec Corp | 光干渉計 |
| JPS61280429A (ja) | 1985-06-06 | 1986-12-11 | Chugai Pharmaceut Co Ltd | 免疫抑制剤 |
| JPH02250828A (ja) | 1989-03-23 | 1990-10-08 | Nippon Kayaku Co Ltd | 新規免疫抑制剤 |
| JPH0586374A (ja) | 1991-09-26 | 1993-04-06 | Teikoku Sekiyu Kk | 炭水化物を可燃性のガスに分解する方法 |
| GB9326284D0 (en) | 1993-12-23 | 1994-02-23 | Erba Carlo Spa | Pyrrolydenemethyl-derivatives and process for their preparation |
| JPH0930967A (ja) | 1995-07-17 | 1997-02-04 | Chugai Pharmaceut Co Ltd | 抗潰瘍剤 |
| GB9603212D0 (en) | 1996-02-15 | 1996-04-17 | Pharmacia Spa | Process for the preparation of 2,2'-bipyrrolyl-pyrromethane derivatives |
| GB9619706D0 (en) | 1996-09-20 | 1996-11-06 | Pharmacia Spa | Synergistic immunosuppressant composition containing a 2,2'-bi-1H-pyrrole comp und |
| JP3949196B2 (ja) | 1996-10-23 | 2007-07-25 | 赤穂化成株式会社 | 免疫抑制剤 |
| JP3949198B2 (ja) | 1996-10-23 | 2007-07-25 | 赤穂化成株式会社 | Ｖ−ＡＴＰａｓｅ 脱共役 Ｈ＋ ポンプ阻害剤 |
| GB9705035D0 (en) | 1997-03-11 | 1997-04-30 | Pharmacia & Upjohn Spa | Indolyl-pyrrolydenemethylpyrrole derivatives and process for their preparation |
| KR100252197B1 (ko) | 1997-09-20 | 2000-04-15 | 박호군 | 세라시아 마르세센스 균주의 배양액으로 부터 분리한 면역억제제용 프로디지오신 |
| JPH11209283A (ja) | 1997-10-01 | 1999-08-03 | Ako Kasei Co Ltd | 抗癌剤 |
| GB9726130D0 (en) | 1997-12-10 | 1998-02-11 | Pharmacia & Upjohn Spa | 2,2'-BI-1H-pyrrole derivatives useful in the treatment of leukemia brought on by HTLV-I |
| GB9802745D0 (en) | 1998-02-09 | 1998-04-08 | Pharmacia & Upjohn Spa | Benzyloxy prodigiosine compounds |
| US6407244B1 (en) | 2000-01-26 | 2002-06-18 | Gemin X Biotechnologies Inc. | Pyrrole-type compounds, compositions, and methods for treating cancer or viral diseases |
-
2000
- 2000-01-26 US US09/491,712 patent/US6407244B1/en not_active Expired - Lifetime
-
2001
- 2001-01-24 CZ CZ20022604A patent/CZ20022604A3/cs unknown
- 2001-01-24 PL PL01356932A patent/PL356932A1/xx not_active Application Discontinuation
- 2001-01-24 EP EP04003643A patent/EP1431286A3/de not_active Withdrawn
- 2001-01-24 IL IL15081701A patent/IL150817A0/xx unknown
- 2001-01-24 AT AT01902193T patent/ATE269859T1/de not_active IP Right Cessation
- 2001-01-24 SK SK1095-2002A patent/SK10952002A3/sk unknown
- 2001-01-24 AU AU29912/01A patent/AU780647B2/en not_active Ceased
- 2001-01-24 DE DE60103978T patent/DE60103978D1/de not_active Expired - Lifetime
- 2001-01-24 JP JP2001560990A patent/JP2003523352A/ja active Pending
- 2001-01-24 MX MXPA02007271A patent/MXPA02007271A/es active IP Right Grant
- 2001-01-24 NZ NZ520361A patent/NZ520361A/en unknown
- 2001-01-24 KR KR1020027009667A patent/KR20020072295A/ko not_active Application Discontinuation
- 2001-01-24 CN CN01807066A patent/CN1419553A/zh active Pending
- 2001-01-24 BR BR0107912-3A patent/BR0107912A/pt not_active IP Right Cessation
- 2001-01-24 EP EP01902193A patent/EP1255753B1/de not_active Expired - Lifetime
- 2001-01-24 CA CA002398173A patent/CA2398173A1/en not_active Abandoned
- 2001-01-24 WO PCT/CA2001/000085 patent/WO2001055131A2/en active IP Right Grant
-
2002
- 2002-04-04 US US10/116,094 patent/US6602879B2/en not_active Expired - Lifetime
- 2002-07-22 ZA ZA200205838A patent/ZA200205838B/en unknown
- 2002-07-22 NO NO20023486A patent/NO20023486L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU780647B2 (en) | 2005-04-07 |
| EP1255753B1 (de) | 2004-06-23 |
| US6602879B2 (en) | 2003-08-05 |
| DE60103978D1 (de) | 2004-07-29 |
| US6407244B1 (en) | 2002-06-18 |
| EP1431286A3 (de) | 2004-07-28 |
| MXPA02007271A (es) | 2004-07-30 |
| EP1431286A2 (de) | 2004-06-23 |
| PL356932A1 (en) | 2004-07-12 |
| AU2991201A (en) | 2001-08-07 |
| BR0107912A (pt) | 2002-12-10 |
| JP2003523352A (ja) | 2003-08-05 |
| KR20020072295A (ko) | 2002-09-14 |
| WO2001055131A2 (en) | 2001-08-02 |
| NO20023486D0 (no) | 2002-07-22 |
| NZ520361A (en) | 2004-02-27 |
| NO20023486L (no) | 2002-09-04 |
| CA2398173A1 (en) | 2001-08-02 |
| ATE269859T1 (de) | 2004-07-15 |
| US20030009032A1 (en) | 2003-01-09 |
| SK10952002A3 (sk) | 2003-01-09 |
| IL150817A0 (en) | 2003-02-12 |
| EP1255753A2 (de) | 2002-11-13 |
| WO2001055131A3 (en) | 2002-03-07 |
| CN1419553A (zh) | 2003-05-21 |
| CZ20022604A3 (cs) | 2003-01-15 |
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