DE2051430A1 - Immunosuppressionsmittel und Antivirusmittel - Google Patents
Immunosuppressionsmittel und AntivirusmittelInfo
- Publication number
- DE2051430A1 DE2051430A1 DE19702051430 DE2051430A DE2051430A1 DE 2051430 A1 DE2051430 A1 DE 2051430A1 DE 19702051430 DE19702051430 DE 19702051430 DE 2051430 A DE2051430 A DE 2051430A DE 2051430 A1 DE2051430 A1 DE 2051430A1
- Authority
- DE
- Germany
- Prior art keywords
- urea
- pyrimidyl
- carbon atoms
- group
- lower alkyl
- 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
- 239000003443 antiviral agent Substances 0.000 title claims description 6
- 229960003444 immunosuppressant agent Drugs 0.000 title claims description 6
- 239000003018 immunosuppressive agent Substances 0.000 title claims description 6
- 229940121357 antivirals Drugs 0.000 title description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- -1 2-pyrimidyl Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 241000700605 Viruses Species 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 101150052863 THY1 gene Proteins 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 230000001861 immunosuppressant effect Effects 0.000 claims 2
- 241000699670 Mus sp. Species 0.000 description 16
- 235000013877 carbamide Nutrition 0.000 description 13
- 238000000034 method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000001506 immunosuppresive effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 206010062016 Immunosuppression Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010033799 Paralysis Diseases 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000035931 haemagglutination Effects 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 description 1
- 208000005777 Lupus Nephritis Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 208000009359 Sezary Syndrome Diseases 0.000 description 1
- 208000021388 Sezary disease Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000008076 immune mechanism Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 201000005737 orchitis Diseases 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNENQQPLJPZMGZ-UHFFFAOYSA-N pyrimidin-2-ylurea Chemical compound NC(=O)NC1=NC=CC=N1 DNENQQPLJPZMGZ-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86707969A | 1969-10-16 | 1969-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2051430A1 true DE2051430A1 (de) | 1971-04-29 |
Family
ID=25349042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702051430 Pending DE2051430A1 (de) | 1969-10-16 | 1970-10-09 | Immunosuppressionsmittel und Antivirusmittel |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164204A1 (en) * | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0512324D0 (en) * | 2005-06-16 | 2005-07-27 | Novartis Ag | Organic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762742A (en) * | 1953-03-11 | 1956-09-11 | Merck & Co Inc | 1-(4-nitro phenyl)-3-(2-pyrimidyl) urea compound for the treatment of coccidiosis and method of preparing the same |
| FR1593586A (enrdf_load_stackoverflow) * | 1967-10-17 | 1970-06-01 |
-
1970
- 1970-10-02 CA CA094,657A patent/CA961855A/en not_active Expired
- 1970-10-02 ZA ZA706704A patent/ZA706704B/xx unknown
- 1970-10-07 IL IL35414A patent/IL35414A/xx unknown
- 1970-10-09 GB GB4823370A patent/GB1316333A/en not_active Expired
- 1970-10-09 DE DE19702051430 patent/DE2051430A1/de active Pending
- 1970-10-14 ES ES384502A patent/ES384502A1/es not_active Expired
- 1970-10-15 AT AT932370A patent/AT308763B/de not_active IP Right Cessation
- 1970-10-15 NL NL7015181A patent/NL7015181A/xx unknown
- 1970-10-15 DK DK525170AA patent/DK124131B/da unknown
- 1970-10-15 JP JP45090854A patent/JPS501275B1/ja active Pending
- 1970-10-16 FR FR7037446A patent/FR2070136B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164204A1 (en) * | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1316333A (en) | 1973-05-09 |
| AT308763B (de) | 1973-07-25 |
| IL35414A0 (en) | 1971-04-28 |
| ZA706704B (en) | 1972-05-31 |
| NL7015181A (enrdf_load_stackoverflow) | 1971-04-20 |
| JPS501275B1 (enrdf_load_stackoverflow) | 1975-01-16 |
| FR2070136A1 (enrdf_load_stackoverflow) | 1971-09-10 |
| IL35414A (en) | 1974-10-22 |
| CA961855A (en) | 1975-01-28 |
| DK124131B (da) | 1972-09-18 |
| FR2070136B1 (enrdf_load_stackoverflow) | 1975-01-10 |
| ES384502A1 (es) | 1973-01-16 |
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