NL8004466A - Heterocyclische koolstofverbindingen met therapeutische eigenschappen. - Google Patents
Heterocyclische koolstofverbindingen met therapeutische eigenschappen. Download PDFInfo
- Publication number
- NL8004466A NL8004466A NL8004466A NL8004466A NL8004466A NL 8004466 A NL8004466 A NL 8004466A NL 8004466 A NL8004466 A NL 8004466A NL 8004466 A NL8004466 A NL 8004466A NL 8004466 A NL8004466 A NL 8004466A
- Authority
- NL
- Netherlands
- Prior art keywords
- adenine
- cyclohexyl
- formula
- cyclohexenyl
- carbon atoms
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001722 carbon compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- -1 2-cyclohexenyl Chemical group 0.000 claims description 23
- 229960000643 adenine Drugs 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 230000003182 bronchodilatating effect Effects 0.000 claims description 7
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- 239000011591 potassium Chemical group 0.000 claims description 4
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- MWEGGBQTDLNNIK-UHFFFAOYSA-N 9-(oxan-2-yl)-2-propoxypurin-6-amine Chemical compound C12=NC(OCCC)=NC(N)=C2N=CN1C1CCCCO1 MWEGGBQTDLNNIK-UHFFFAOYSA-N 0.000 claims description 3
- QGWMOSLEZZMDEV-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-n-propylpurine-2,6-diamine Chemical compound C12=NC(NCCC)=NC(N)=C2N=CN1C1CCCC=C1 QGWMOSLEZZMDEV-UHFFFAOYSA-N 0.000 claims description 3
- CVRZGPWTMFDLPX-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-propylsulfanylpurin-6-amine Chemical compound C12=NC(SCCC)=NC(N)=C2N=CN1C1CCCC=C1 CVRZGPWTMFDLPX-UHFFFAOYSA-N 0.000 claims description 3
- NWLXPUMKAKIHNI-UHFFFAOYSA-N 9-cyclohexyl-2-n-propylpurine-2,6-diamine Chemical compound C12=NC(NCCC)=NC(N)=C2N=CN1C1CCCCC1 NWLXPUMKAKIHNI-UHFFFAOYSA-N 0.000 claims description 3
- QPNGFALSNMHJPQ-UHFFFAOYSA-N 9-cyclohexyl-2-propylsulfanylpurin-6-amine Chemical compound C12=NC(SCCC)=NC(N)=C2N=CN1C1CCCCC1 QPNGFALSNMHJPQ-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002367 halogens Chemical group 0.000 claims description 3
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
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- 229910052744 lithium Inorganic materials 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
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- 229910000573 alkali metal alloy Inorganic materials 0.000 claims 1
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 description 4
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- 125000005059 halophenyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
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- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical group BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 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
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- POFWRMVFWIJXHP-UHFFFAOYSA-N n-benzyl-9-(oxan-2-yl)purin-6-amine Chemical compound C=1C=CC=CC=1CNC(C=1N=C2)=NC=NC=1N2C1CCCCO1 POFWRMVFWIJXHP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000005062 tracheal ring Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/064,240 US4241063A (en) | 1979-08-06 | 1979-08-06 | Purine derivatives and their use as bronchodilators |
| US6424079 | 1979-08-06 | ||
| US06/074,848 US4269839A (en) | 1979-09-13 | 1979-09-13 | Alkylthio-adenines used as bronchodilators |
| US7484879 | 1979-09-13 | ||
| US7484979 | 1979-09-13 | ||
| US06/074,849 US4232155A (en) | 1979-09-13 | 1979-09-13 | Purine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004466A true NL8004466A (nl) | 1981-02-10 |
Family
ID=27370586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004466A NL8004466A (nl) | 1979-08-06 | 1980-08-05 | Heterocyclische koolstofverbindingen met therapeutische eigenschappen. |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996011200A1 (en) * | 1994-10-05 | 1996-04-18 | Chiroscience Limited | Purine and guanine compounds as inhibitors of pnp |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1405548A (fr) * | 1963-07-17 | 1965-07-09 | Shell Int Research | Procédé pour favoiriser la croissance ou pour empêcher les processus de décomposition des plantes ou des tissus des plantes |
| US4172829A (en) * | 1978-05-09 | 1979-10-30 | Bristol-Myers Company | 2,9-Disubstituted adenine derivatives and their use as non-adrenergic bronchodilators |
-
1980
- 1980-07-31 FI FI802401A patent/FI802401A7/fi not_active Application Discontinuation
- 1980-08-01 FR FR8017104A patent/FR2463142A1/fr not_active Withdrawn
- 1980-08-04 GB GB8025320A patent/GB2056448A/en not_active Withdrawn
- 1980-08-05 GR GR62609A patent/GR76109B/el unknown
- 1980-08-05 IT IT49425/80A patent/IT1188987B/it active
- 1980-08-05 NL NL8004466A patent/NL8004466A/nl not_active Application Discontinuation
- 1980-08-05 SE SE8005558A patent/SE8005558L/xx unknown
- 1980-08-05 DK DK337680A patent/DK337680A/da unknown
- 1980-08-05 YU YU1970/80A patent/YU45101B/xx unknown
- 1980-08-06 LU LU82694A patent/LU82694A1/fr unknown
- 1980-08-06 DE DE19803029806 patent/DE3029806A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2056448A (en) | 1981-03-18 |
| DK337680A (da) | 1981-02-07 |
| YU197080A (en) | 1990-04-30 |
| SE8005558L (sv) | 1981-02-07 |
| FR2463142A1 (fr) | 1981-02-20 |
| DE3029806A1 (de) | 1981-03-26 |
| GR76109B (enrdf_load_stackoverflow) | 1984-08-03 |
| LU82694A1 (fr) | 1981-03-24 |
| IT8049425A0 (it) | 1980-08-05 |
| FI802401A7 (fi) | 1981-01-01 |
| IT8049425A1 (it) | 1982-02-05 |
| IT1188987B (it) | 1988-01-28 |
| YU45101B (en) | 1992-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |