JPS6228954B2 - - Google Patents
Info
- Publication number
- JPS6228954B2 JPS6228954B2 JP55181776A JP18177680A JPS6228954B2 JP S6228954 B2 JPS6228954 B2 JP S6228954B2 JP 55181776 A JP55181776 A JP 55181776A JP 18177680 A JP18177680 A JP 18177680A JP S6228954 B2 JPS6228954 B2 JP S6228954B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carboxyborane
- compound
- represent
- methyl group
- 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
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- WXLFRZRGSPLPEW-UHFFFAOYSA-N boranylformic acid;n,n-dimethylmethanamine Chemical compound BC(O)=O.CN(C)C WXLFRZRGSPLPEW-UHFFFAOYSA-N 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 4
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 230000001315 anti-hyperlipaemic effect Effects 0.000 abstract description 12
- 150000001638 boron Chemical class 0.000 abstract description 12
- 230000000259 anti-tumor effect Effects 0.000 abstract description 11
- 150000001413 amino acids Chemical class 0.000 abstract description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 25
- 229910002091 carbon monoxide Inorganic materials 0.000 description 25
- 239000013078 crystal Substances 0.000 description 17
- RRMCILTYBQCEHE-UHFFFAOYSA-N boranylformic acid;methanamine Chemical compound NC.BC(O)=O RRMCILTYBQCEHE-UHFFFAOYSA-N 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 11
- BTSWWBIRVRVZNU-UHFFFAOYSA-N boranylformic acid;n-methylmethanamine Chemical compound CNC.BC(O)=O BTSWWBIRVRVZNU-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 230000004071 biological effect Effects 0.000 description 7
- -1 carboxyborane - Ammonia-carboxyborane Chemical compound 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- MUTDNIUYABKXLN-UHFFFAOYSA-N azane;boranylformic acid Chemical compound [NH4+].BC([O-])=O MUTDNIUYABKXLN-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 5
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 5
- 108010077895 Sarcosine Proteins 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 206010003445 Ascites Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229940043230 sarcosine Drugs 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 108700003601 dimethylglycine Proteins 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
- 229940078490 n,n-dimethylglycine Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000005891 transamination reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000004607 11B NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- KOXIGEBRUGYXFD-UHFFFAOYSA-N boranylformic acid Chemical compound BC(O)=O KOXIGEBRUGYXFD-UHFFFAOYSA-N 0.000 description 1
- 238000001897 boron-11 nuclear magnetic resonance spectrum 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
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10641679A | 1979-12-21 | 1979-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57145886A JPS57145886A (en) | 1982-09-09 |
| JPS6228954B2 true JPS6228954B2 (online.php) | 1987-06-23 |
Family
ID=22311304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55181776A Granted JPS57145886A (en) | 1979-12-21 | 1980-12-22 | Novel amine-carboxyborane, manufacture and anticancer and antihyperlipemic comprising same |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0034238B1 (online.php) |
| JP (1) | JPS57145886A (online.php) |
| AT (1) | ATE12774T1 (online.php) |
| DE (1) | DE3070534D1 (online.php) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6299384A (ja) * | 1984-10-25 | 1987-05-08 | デユ−ク・ユニヴア−シテイ | （ｃｈ↓３）↓３ｎｂｈ↓２ｃｏｏｃｈ↓３を含む脂血低下剤 |
| US4647555A (en) * | 1984-10-25 | 1987-03-03 | The United States Of America As Represented By The Secretary Of The Army | Esters of boron analogues of amino acids |
| US4740504A (en) * | 1985-10-08 | 1988-04-26 | United States Borax & Chemical Corp. | Antihyperlipidemic amine boranes |
| US4672060A (en) * | 1985-10-18 | 1987-06-09 | United States Borax & Chemical Corporation | Antihyperlipidemic ammonium polyboranes |
| US4977268A (en) * | 1988-04-08 | 1990-12-11 | Duke University | Boron dipeptide compounds |
| US5023513A (en) * | 1989-06-09 | 1991-06-11 | Boron Biologicals, Inc. | Amine-alkylborane derivatives and methods |
| US5143907A (en) * | 1991-05-10 | 1992-09-01 | Boron Biologicals, Inc. | Phosphite-borane compounds, and method of making and using the same |
| US5260427A (en) * | 1991-05-10 | 1993-11-09 | Boron Biolgicals, Inc. | Nucleosidylphosphite-borane compounds and method of making the same |
| HU226659B1 (en) * | 1999-10-05 | 2009-06-29 | Mallinckrodt Inc | Carbon monoxide source for preparation of transition-metal-carbonyl-complexes |
| GB0111872D0 (en) | 2001-05-15 | 2001-07-04 | Northwick Park Inst For Medica | Therapeutic agents and methods |
| EP2042181A1 (en) | 2002-02-04 | 2009-04-01 | ALFAMA-Investigacao e Desenvolvimento de Produtos Farmaceuticos Lda. | Use of co-releasing compounds for the manufacture of a medicament for the treatment of inflammatory diseases |
| US7968605B2 (en) | 2002-02-04 | 2011-06-28 | ALFAMA—Investigação e Desenvolvimento de Produtos Farmacêuticos, Lda. | Methods for treating inflammatory disease by administering aldehydes and derivatives thereof |
| WO2007032004A1 (en) * | 2005-09-13 | 2007-03-22 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Use of amine-borane compounds as anti-microbial agents |
| GB0601394D0 (en) | 2006-01-24 | 2006-03-01 | Hemocorm Ltd | Therapeutic delivery of carbon monoxide |
| US9163044B2 (en) | 2011-04-19 | 2015-10-20 | Alfama, Inc. | Carbon monoxide releasing molecules and uses thereof |
| WO2013013179A1 (en) | 2011-07-21 | 2013-01-24 | Alfama, Inc. | Ruthenium carbon monoxide releasing molecules and uses thereof |
-
1980
- 1980-12-19 AT AT80810406T patent/ATE12774T1/de not_active IP Right Cessation
- 1980-12-19 DE DE8080810406T patent/DE3070534D1/de not_active Expired
- 1980-12-19 EP EP80810406A patent/EP0034238B1/en not_active Expired
- 1980-12-22 JP JP55181776A patent/JPS57145886A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0034238B1 (en) | 1985-04-17 |
| EP0034238A1 (en) | 1981-08-26 |
| DE3070534D1 (en) | 1985-05-23 |
| ATE12774T1 (de) | 1985-05-15 |
| JPS57145886A (en) | 1982-09-09 |
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