NO318801B1 - Hiv-replikasjonsinhiberende pyrimidiner, dens anvendelse, farmasoytiske sammensetninger inneholder dem og fremgangsmate for deres fremstilling - Google Patents
Hiv-replikasjonsinhiberende pyrimidiner, dens anvendelse, farmasoytiske sammensetninger inneholder dem og fremgangsmate for deres fremstilling Download PDFInfo
- Publication number
- NO318801B1 NO318801B1 NO20011696A NO20011696A NO318801B1 NO 318801 B1 NO318801 B1 NO 318801B1 NO 20011696 A NO20011696 A NO 20011696A NO 20011696 A NO20011696 A NO 20011696A NO 318801 B1 NO318801 B1 NO 318801B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- formula
- alkyl
- compound
- benzonitrile
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000002401 inhibitory effect Effects 0.000 title description 5
- 150000003230 pyrimidines Chemical class 0.000 title description 4
- 230000010076 replication Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 133
- 239000002904 solvent Substances 0.000 claims description 56
- -1 cyano, aminocarbonyl Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 18
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 150000001412 amines Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 229910052736 halogen Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 239000012298 atmosphere Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
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- 208000015181 infectious disease Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 4
- GNELAKVSOPMFKN-UHFFFAOYSA-N 4-[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br GNELAKVSOPMFKN-UHFFFAOYSA-N 0.000 claims description 3
- VKQKEROEGYSHIY-UHFFFAOYSA-N 4-[[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]amino]-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br VKQKEROEGYSHIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 230000036436 anti-hiv Effects 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- WPNAIKSJHKWRNV-UHFFFAOYSA-N 4-[6-amino-5-chloro-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Cl WPNAIKSJHKWRNV-UHFFFAOYSA-N 0.000 claims description 2
- SWJAAIMAEBSKQZ-UHFFFAOYSA-N 4-[[4-amino-5-chloro-6-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Cl SWJAAIMAEBSKQZ-UHFFFAOYSA-N 0.000 claims description 2
- SOJXDRPTMGPTRD-UHFFFAOYSA-N 4-[[5-chloro-4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Cl SOJXDRPTMGPTRD-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D403/02—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 two hetero rings
- C07D403/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
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- 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
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- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10779298P | 1998-11-10 | 1998-11-10 | |
| US14396299P | 1999-07-15 | 1999-07-15 | |
| PCT/EP1999/007417 WO2000027825A1 (fr) | 1998-11-10 | 1999-09-24 | Pyrimidines inhibant la replication du vih |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011696D0 NO20011696D0 (no) | 2001-04-04 |
| NO20011696L NO20011696L (no) | 2001-04-04 |
| NO318801B1 true NO318801B1 (no) | 2005-05-09 |
Family
ID=26805159
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011696A NO318801B1 (no) | 1998-11-10 | 2001-04-04 | Hiv-replikasjonsinhiberende pyrimidiner, dens anvendelse, farmasoytiske sammensetninger inneholder dem og fremgangsmate for deres fremstilling |
| NO2009003C NO2009003I2 (no) | 1998-11-10 | 2009-02-23 | Etravirin |
| NO2021015C NO2021015I1 (no) | 1998-11-10 | 2021-03-29 | Etravirin - forlenget SPC |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2009003C NO2009003I2 (no) | 1998-11-10 | 2009-02-23 | Etravirin |
| NO2021015C NO2021015I1 (no) | 1998-11-10 | 2021-03-29 | Etravirin - forlenget SPC |
Country Status (41)
| Country | Link |
|---|---|
| US (5) | US6878717B2 (fr) |
| EP (2) | EP1270560B1 (fr) |
| JP (1) | JP3635238B2 (fr) |
| KR (1) | KR100658489B1 (fr) |
| CN (1) | CN1214013C (fr) |
| AP (1) | AP1683A (fr) |
| AR (1) | AR024227A1 (fr) |
| AT (2) | ATE233740T1 (fr) |
| AU (2) | AU762523C (fr) |
| BG (1) | BG65103B1 (fr) |
| BR (1) | BRPI9915552B8 (fr) |
| CA (1) | CA2350801C (fr) |
| CY (1) | CY2008021I1 (fr) |
| CZ (1) | CZ301367B6 (fr) |
| DE (3) | DE122009000003I1 (fr) |
| DK (1) | DK1002795T3 (fr) |
| EA (1) | EA004049B1 (fr) |
| EE (1) | EE05086B1 (fr) |
| ES (2) | ES2338760T3 (fr) |
| FR (1) | FR09C0004I2 (fr) |
| HK (2) | HK1025330A1 (fr) |
| HR (2) | HRP20010161B9 (fr) |
| HU (2) | HU230394B1 (fr) |
| ID (1) | ID28376A (fr) |
| IL (2) | IL143023A0 (fr) |
| LT (1) | LTC1002795I2 (fr) |
| LU (1) | LU91528I2 (fr) |
| MY (1) | MY121108A (fr) |
| NL (1) | NL300373I2 (fr) |
| NO (3) | NO318801B1 (fr) |
| NZ (1) | NZ511116A (fr) |
| OA (1) | OA11674A (fr) |
| PL (1) | PL204427B1 (fr) |
| PT (1) | PT1002795E (fr) |
| SI (1) | SI1002795T1 (fr) |
| SK (2) | SK287269B6 (fr) |
| TR (1) | TR200101306T2 (fr) |
| TW (1) | TWI238161B (fr) |
| UA (1) | UA70966C2 (fr) |
| WO (1) | WO2000027825A1 (fr) |
| ZA (1) | ZA200103769B (fr) |
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