DE2241470A1 - Arzneimittel mit antivirus-wirksamkeit - Google Patents
Arzneimittel mit antivirus-wirksamkeitInfo
- Publication number
- DE2241470A1 DE2241470A1 DE19722241470 DE2241470A DE2241470A1 DE 2241470 A1 DE2241470 A1 DE 2241470A1 DE 19722241470 DE19722241470 DE 19722241470 DE 2241470 A DE2241470 A DE 2241470A DE 2241470 A1 DE2241470 A1 DE 2241470A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- virus
- acetylchlorophenyl
- nhcsnh
- thiourea
- 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.)
- Withdrawn
Links
- 230000002155 anti-virotic effect Effects 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 fatty acid radical Chemical class 0.000 claims description 37
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 241000700605 Viruses Species 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 17
- 230000000840 anti-viral effect Effects 0.000 description 14
- 150000003585 thioureas Chemical class 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 241000709677 Coxsackievirus B1 Species 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 241000217423 Echovirus E19 Species 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 241000709701 Human poliovirus 1 Species 0.000 description 5
- 239000013068 control sample Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 239000000902 placebo Substances 0.000 description 5
- 229940068196 placebo Drugs 0.000 description 5
- 208000007212 Foot-and-Mouth Disease Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 208000030194 mouth disease Diseases 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BTFREYNHBKXMCJ-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-3-phenylthiourea Chemical compound OC1=CC=CC(NC(=S)NC=2C=CC=CC=2)=C1 BTFREYNHBKXMCJ-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000709664 Picornaviridae Species 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- MHKFCCJUQZAXSH-UHFFFAOYSA-N 1-(3-methylphenyl)-3-phenylthiourea Chemical compound CC1=CC=CC(NC(=S)NC=2C=CC=CC=2)=C1 MHKFCCJUQZAXSH-UHFFFAOYSA-N 0.000 description 1
- DMGXHAJMRPAATB-UHFFFAOYSA-N 2-(phenylcarbamothioylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=S)NC1=CC=CC=C1 DMGXHAJMRPAATB-UHFFFAOYSA-N 0.000 description 1
- QIYIZFXGUVHGKZ-UHFFFAOYSA-N 2-hydroxy-4-(phenylcarbamothioylamino)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1NC(=S)NC1=CC=CC=C1 QIYIZFXGUVHGKZ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001669084 Coxsackievirus A6 Species 0.000 description 1
- 241000146321 Coxsackievirus A7 Species 0.000 description 1
- 241000709675 Coxsackievirus B3 Species 0.000 description 1
- 241001466953 Echovirus Species 0.000 description 1
- 241000988559 Enterovirus A Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 241000709704 Human poliovirus 2 Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- TTZUCVNWOZLIGL-UHFFFAOYSA-N chembl362994 Chemical class C1=CC=C2N(C)C(O)=C(N=NC(S)=N)C2=C1 TTZUCVNWOZLIGL-UHFFFAOYSA-N 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000005723 virus inoculator Substances 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG1729471 | 1971-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2241470A1 true DE2241470A1 (de) | 1973-03-22 |
Family
ID=3897739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722241470 Withdrawn DE2241470A1 (de) | 1971-08-23 | 1972-08-23 | Arzneimittel mit antivirus-wirksamkeit |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS4828609A (enExample) |
| DE (1) | DE2241470A1 (enExample) |
| FR (1) | FR2150834B1 (enExample) |
| GB (1) | GB1408198A (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5780483A (en) * | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US5886044A (en) * | 1995-02-17 | 1999-03-23 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6005008A (en) * | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6133319A (en) * | 1996-06-27 | 2000-10-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6211373B1 (en) | 1996-03-20 | 2001-04-03 | Smithkline Beecham Corporation | Phenyl urea antagonists of the IL-8 receptor |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6271261B1 (en) | 1996-06-27 | 2001-08-07 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA010017B1 (ru) * | 2003-07-10 | 2008-06-30 | Ачиллион Фармасьютикалз, Инк. | Замещённые арилтиомочевины, применимые в качестве ингибиторов репликации вирусов |
| TW200528459A (en) * | 2004-01-06 | 2005-09-01 | Achillion Pharmaceuticals Inc | Azabenzofuran substituted thioureas; inhibitors of viral replication |
-
1972
- 1972-08-23 GB GB3933572A patent/GB1408198A/en not_active Expired
- 1972-08-23 DE DE19722241470 patent/DE2241470A1/de not_active Withdrawn
- 1972-08-23 JP JP8442572A patent/JPS4828609A/ja active Pending
- 1972-08-23 FR FR7230066A patent/FR2150834B1/fr not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5780483A (en) * | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US5886044A (en) * | 1995-02-17 | 1999-03-23 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6180675B1 (en) | 1995-02-17 | 2001-01-30 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6005008A (en) * | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6211373B1 (en) | 1996-03-20 | 2001-04-03 | Smithkline Beecham Corporation | Phenyl urea antagonists of the IL-8 receptor |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6133319A (en) * | 1996-06-27 | 2000-10-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6271261B1 (en) | 1996-06-27 | 2001-08-07 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4828609A (enExample) | 1973-04-16 |
| FR2150834B1 (enExample) | 1975-10-17 |
| GB1408198A (en) | 1975-10-01 |
| FR2150834A1 (enExample) | 1973-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS |
|
| 8139 | Disposal/non-payment of the annual fee |