CH645633A5 - Process for the preparation of hydroxylated derivatives of isopropylaminopyrimidine - Google Patents
Process for the preparation of hydroxylated derivatives of isopropylaminopyrimidine Download PDFInfo
- Publication number
- CH645633A5 CH645633A5 CH268980A CH268980A CH645633A5 CH 645633 A5 CH645633 A5 CH 645633A5 CH 268980 A CH268980 A CH 268980A CH 268980 A CH268980 A CH 268980A CH 645633 A5 CH645633 A5 CH 645633A5
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropylamino
- hydrogen atom
- preparation
- isopropylaminopyrimidine
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- FTCYIGBVOHNHCD-UHFFFAOYSA-N isaxonine Chemical class CC(C)NC1=NC=CC=N1 FTCYIGBVOHNHCD-UHFFFAOYSA-N 0.000 title abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- AVRNZAITOUMSPB-UHFFFAOYSA-N 4-propan-2-ylpyrimidin-2-amine Chemical class CC(C)C1=CC=NC(N)=N1 AVRNZAITOUMSPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 201000006938 muscular dystrophy Diseases 0.000 abstract description 2
- 230000007823 neuropathy Effects 0.000 abstract description 2
- 201000001119 neuropathy Diseases 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 210000003497 sciatic nerve Anatomy 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- UBGRSKXBCVWAOV-UHFFFAOYSA-N 2-(propan-2-ylamino)pyrimidin-5-ol Chemical compound CC(C)NC1=NC=C(O)C=N1 UBGRSKXBCVWAOV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7914987 | 1979-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH645633A5 true CH645633A5 (en) | 1984-10-15 |
Family
ID=10504858
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268980A CH645633A5 (en) | 1979-04-30 | 1980-04-08 | Process for the preparation of hydroxylated derivatives of isopropylaminopyrimidine |
| CH269080A CH645361A5 (en) | 1979-04-30 | 1980-04-08 | Process for the preparation of hydroxylated derivatives of isopropylaminopyrimidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH269080A CH645361A5 (en) | 1979-04-30 | 1980-04-08 | Process for the preparation of hydroxylated derivatives of isopropylaminopyrimidine |
Country Status (26)
| Country | Link |
|---|---|
| JP (2) | JPS55145670A (de) |
| AR (2) | AR222869A1 (de) |
| AT (2) | AT380013B (de) |
| BE (2) | BE882593A (de) |
| CH (2) | CH645633A5 (de) |
| DK (2) | DK183780A (de) |
| EG (2) | EG14284A (de) |
| ES (2) | ES8103060A1 (de) |
| FI (2) | FI66358C (de) |
| FR (2) | FR2455588A1 (de) |
| GB (2) | GB2055801B (de) |
| HK (2) | HK55583A (de) |
| IE (2) | IE49709B1 (de) |
| IN (2) | IN154066B (de) |
| IT (2) | IT1141296B (de) |
| LU (2) | LU82332A1 (de) |
| MA (1) | MA18824A1 (de) |
| MX (2) | MX6514E (de) |
| MY (2) | MY8400204A (de) |
| NL (2) | NL8002271A (de) |
| NO (2) | NO154055C (de) |
| NZ (2) | NZ193421A (de) |
| OA (2) | OA06525A (de) |
| PT (2) | PT71155A (de) |
| SG (2) | SG22283G (de) |
| ZA (2) | ZA801958B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63145595U (de) * | 1987-03-13 | 1988-09-26 | ||
| JPS645795U (de) * | 1987-06-26 | 1989-01-13 | ||
| JPH01100695U (de) * | 1987-12-21 | 1989-07-06 | ||
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
| USD500447S1 (en) * | 2003-08-07 | 2005-01-04 | Kranson Industries | Oval bottle |
| USD505864S1 (en) * | 2003-08-07 | 2005-06-07 | Kranson Industries | Oval bottle |
-
1980
- 1980-04-02 ZA ZA00801958A patent/ZA801958B/xx unknown
- 1980-04-02 BE BE0/200083A patent/BE882593A/fr not_active IP Right Cessation
- 1980-04-02 ZA ZA00801960A patent/ZA801960B/xx unknown
- 1980-04-02 BE BE0/200084A patent/BE882594A/fr not_active IP Right Cessation
- 1980-04-03 FI FI801083A patent/FI66358C/fi not_active IP Right Cessation
- 1980-04-03 FI FI801084A patent/FI66359C/fi not_active IP Right Cessation
- 1980-04-03 LU LU82332A patent/LU82332A1/fr unknown
- 1980-04-03 LU LU82333A patent/LU82333A1/fr unknown
- 1980-04-07 IN IN253/DEL/80A patent/IN154066B/en unknown
- 1980-04-07 IN IN254/DEL/80A patent/IN154067B/en unknown
- 1980-04-08 CH CH268980A patent/CH645633A5/fr not_active IP Right Cessation
- 1980-04-08 CH CH269080A patent/CH645361A5/fr not_active IP Right Cessation
- 1980-04-11 NZ NZ193421A patent/NZ193421A/xx unknown
- 1980-04-11 NZ NZ193422A patent/NZ193422A/xx unknown
- 1980-04-15 GB GB8012351A patent/GB2055801B/en not_active Expired
- 1980-04-15 GB GB8012349A patent/GB2054556B/en not_active Expired
- 1980-04-18 NL NL8002271A patent/NL8002271A/nl unknown
- 1980-04-18 NL NL8002272A patent/NL8002272A/nl not_active Application Discontinuation
- 1980-04-22 IT IT21543/80A patent/IT1141296B/it active
- 1980-04-22 IT IT21542/80A patent/IT1141487B/it active
- 1980-04-22 MA MA19019A patent/MA18824A1/fr unknown
- 1980-04-24 AT AT0221680A patent/AT380013B/de not_active IP Right Cessation
- 1980-04-24 AT AT0221580A patent/AT380012B/de not_active IP Right Cessation
- 1980-04-25 AR AR280810A patent/AR222869A1/es active
- 1980-04-25 AR AR280811A patent/AR222870A1/es active
- 1980-04-28 NO NO801234A patent/NO154055C/no unknown
- 1980-04-28 MX MX808783U patent/MX6514E/es unknown
- 1980-04-28 MX MX808786U patent/MX5878E/es unknown
- 1980-04-28 PT PT71155A patent/PT71155A/pt unknown
- 1980-04-28 JP JP5557480A patent/JPS55145670A/ja active Granted
- 1980-04-28 IE IE865/80A patent/IE49709B1/en unknown
- 1980-04-28 PT PT71154A patent/PT71154A/pt unknown
- 1980-04-28 IE IE864/80A patent/IE49591B1/en unknown
- 1980-04-28 NO NO801235A patent/NO154056C/no unknown
- 1980-04-28 JP JP5557580A patent/JPS55145671A/ja active Granted
- 1980-04-29 DK DK183780A patent/DK183780A/da unknown
- 1980-04-29 DK DK183880A patent/DK183880A/da unknown
- 1980-04-29 ES ES490999A patent/ES8103060A1/es not_active Expired
- 1980-04-29 EG EG257/80A patent/EG14284A/xx active
- 1980-04-29 ES ES491000A patent/ES491000A0/es active Granted
- 1980-04-29 EG EG258/80A patent/EG14259A/xx active
- 1980-04-30 OA OA57101A patent/OA06525A/xx unknown
- 1980-04-30 OA OA57103A patent/OA06527A/xx unknown
- 1980-04-30 FR FR8009732A patent/FR2455588A1/fr active Granted
- 1980-04-30 FR FR8009733A patent/FR2455589A1/fr active Granted
-
1983
- 1983-04-28 SG SG222/83A patent/SG22283G/en unknown
- 1983-04-28 SG SG225/83A patent/SG22583G/en unknown
- 1983-11-17 HK HK555/83A patent/HK55583A/xx unknown
- 1983-11-17 HK HK556/83A patent/HK55683A/xx unknown
-
1984
- 1984-12-30 MY MY204/84A patent/MY8400204A/xx unknown
- 1984-12-30 MY MY203/84A patent/MY8400203A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |