ZA200100457B - Nitric esters and nitrate salts of specific drugs. - Google Patents
Nitric esters and nitrate salts of specific drugs. Download PDFInfo
- Publication number
- ZA200100457B ZA200100457B ZA200100457A ZA200100457A ZA200100457B ZA 200100457 B ZA200100457 B ZA 200100457B ZA 200100457 A ZA200100457 A ZA 200100457A ZA 200100457 A ZA200100457 A ZA 200100457A ZA 200100457 B ZA200100457 B ZA 200100457B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- salt
- nitrate
- pct
- salts
- Prior art date
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- 150000002823 nitrates Chemical class 0.000 title claims description 31
- 239000003814 drug Substances 0.000 title claims description 11
- 229940079593 drug Drugs 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000000243 solution Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 229960002052 salbutamol Drugs 0.000 claims description 17
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 14
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 229960005174 ambroxol Drugs 0.000 claims description 9
- 229960001803 cetirizine Drugs 0.000 claims description 8
- 229960001985 dextromethorphan Drugs 0.000 claims description 8
- 230000007170 pathology Effects 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- 229960000325 emedastine Drugs 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 claims description 6
- 229960003870 bromhexine Drugs 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229960003088 loratadine Drugs 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229960000351 terfenadine Drugs 0.000 claims description 5
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 claims description 4
- KBUZBQVCBVDWKX-UHFFFAOYSA-N emedastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1N1CCCN(C)CC1 KBUZBQVCBVDWKX-UHFFFAOYSA-N 0.000 claims description 4
- 229960004958 ketotifen Drugs 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 210000002345 respiratory system Anatomy 0.000 claims description 4
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- 229960004150 aciclovir Drugs 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 239000000043 antiallergic agent Substances 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229960003276 erythromycin Drugs 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229960003350 isoniazid Drugs 0.000 claims description 2
- 229960000282 metronidazole Drugs 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 229960005206 pyrazinamide Drugs 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- -1 Cetrezin Chemical compound 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 229910002651 NO3 Inorganic materials 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 11
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 10
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000012848 Dextrorphan Substances 0.000 description 8
- 229950006878 dextrorphan Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 7
- JAQUASYNZVUNQP-PVAVHDDUSA-N dextrorphan Chemical compound C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 JAQUASYNZVUNQP-PVAVHDDUSA-N 0.000 description 6
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 229960002504 capsaicin Drugs 0.000 description 5
- 235000017663 capsaicin Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 4
- 229960004342 cetirizine hydrochloride Drugs 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 229960004398 nedocromil Drugs 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000019693 Lung disease Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 230000002921 anti-spasmodic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- SNDDIRAXSDUVKW-URVXVIKDSA-N dextromethorphan hcl Chemical compound Cl.C([C@@H]12)CCC[C@]11CCN(C)[C@H]2CC2=CC=C(OC)C=C21 SNDDIRAXSDUVKW-URVXVIKDSA-N 0.000 description 3
- 229960005257 dextromethorphan hydrochloride Drugs 0.000 description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 230000001524 infective effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 208000005189 Embolism Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000001435 Thromboembolism Diseases 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 229940124575 antispasmodic agent Drugs 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 230000002802 cardiorespiratory effect Effects 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- MKMAMQPDRUXVSS-YPYJQMNVSA-N dextrorphan hcl Chemical compound Cl.C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 MKMAMQPDRUXVSS-YPYJQMNVSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- YQSHYGCCYVPRDI-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=C(CN)C=C1 YQSHYGCCYVPRDI-UHFFFAOYSA-N 0.000 description 1
- QNVKOSLOVOTXKF-UHFFFAOYSA-N 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol;hydron;chloride Chemical compound Cl.NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1 QNVKOSLOVOTXKF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000919811 Collyria Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 229960000985 ambroxol hydrochloride Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229960003782 dextromethorphan hydrobromide Drugs 0.000 description 1
- WVFGKGPFQSEWON-YPYJQMNVSA-N dextrorphan hydrobromide Chemical compound Br.C1C2=CC=C(O)C=C2[C@@]23CCN(C)[C@@H]1[C@H]2CCCC3 WVFGKGPFQSEWON-YPYJQMNVSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000213 tachycardiac effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06Q—INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES; SYSTEMS OR METHODS SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES, NOT OTHERWISE PROVIDED FOR
- G06Q20/00—Payment architectures, schemes or protocols
- G06Q20/04—Payment circuits
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
IT1303671B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali dell'acido nitrico con farmaci attivi nel trattamento dipatologie del sistema respiratorio |
IT1317735B1 (it) * | 2000-01-26 | 2003-07-15 | Nicox Sa | Sali di agenti antimicrobici. |
US6642276B2 (en) * | 2001-10-01 | 2003-11-04 | M/S Ind-Swift Limited | Controlled release macrolide pharmaceutical formulations |
US7220749B2 (en) | 2002-06-11 | 2007-05-22 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
EP1539679A4 (fr) * | 2002-06-28 | 2007-07-04 | Nitromed Inc | Inhibiteurs a selectivite cyclooxygenase-2 nitrosiles et/ou nitroses contenant une oxime et/ou une hydrazone, compositions et methodes d'utilisation correspondantes |
GB0406069D0 (en) * | 2004-03-17 | 2004-04-21 | Thompson James | Process |
RU2008100237A (ru) * | 2005-06-14 | 2009-07-20 | Джилид Сайэнс, Инк. (US) | ОБЩИЕ ПРОЛЕКАРСТВЕННЫЕ ФОРМЫ СТЕРОИДОВ И β-АГОНИСТОВ (ВАРИАНТЫ), ВКЛЮЧАЮЩИЙ ИХ АЭРОЗОЛЬНЫЙ СОСТАВ (ВАРИАНТЫ) И СПОСОБ ПРЕДОТВРАЩЕНИЯ И/ИЛИ ЛЕЧЕНИЯ ЛЕГОЧНЫХ ВОСПАЛЕНИЙ И/ИЛИ БРОНХОСТЕНОЗА С ИХ ПОМОЩЬЮ |
TW200804241A (en) * | 2006-02-24 | 2008-01-16 | Novartis Ag | New salt |
JP2007275193A (ja) * | 2006-04-04 | 2007-10-25 | Fujifilm Corp | 光プローブおよび光断層画像化装置 |
WO2009142772A2 (fr) | 2008-05-23 | 2009-11-26 | Mastcell Pharmaceuticals, Inc. | Méthodes et traitement d’allergies et inflammations associées à des pathologies gastro-intestinales |
US8263581B2 (en) | 2009-07-03 | 2012-09-11 | Jdp Therapeutics, Inc. | Non-sedating antihistamine injection formulations and methods of use thereof |
US8513259B2 (en) | 2009-07-03 | 2013-08-20 | Jdp Therapeutics, Inc. | Non-sedating antihistamine injection formulations and methods of use thereof |
JP6042197B2 (ja) * | 2012-12-11 | 2016-12-14 | エア・ウォーター株式会社 | 肺障害治療剤 |
CN104211604B (zh) * | 2014-08-18 | 2016-05-11 | 江苏正大清江制药有限公司 | 一种氨溴索与对羟基苯甲酸的共晶及其制备方法 |
CN104211605B (zh) * | 2014-08-18 | 2016-04-27 | 江苏正大清江制药有限公司 | 一种氨溴索与间羟基苯甲酸共晶及其制备方法 |
WO2018089797A1 (fr) | 2016-11-14 | 2018-05-17 | Mingwu Wang | Formulations destinées au traitement des maladies de la surface oculaire et méthodes associées |
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JPS56113748A (en) * | 1980-02-13 | 1981-09-07 | Kowa Co | Aminoethanol derivative and its preparation |
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IT1303671B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali dell'acido nitrico con farmaci attivi nel trattamento dipatologie del sistema respiratorio |
IT1308633B1 (it) * | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
US6383471B1 (en) * | 1999-04-06 | 2002-05-07 | Lipocine, Inc. | Compositions and methods for improved delivery of ionizable hydrophobic therapeutic agents |
IT1311924B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
IT1311923B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
IT1317735B1 (it) * | 2000-01-26 | 2003-07-15 | Nicox Sa | Sali di agenti antimicrobici. |
US20020137764A1 (en) * | 2000-10-31 | 2002-09-26 | Karin Drechsel | Inhalable formulation of a solution containing a tiotropium salt |
US6479692B1 (en) * | 2001-05-02 | 2002-11-12 | Nobex Corporation | Methods of synthesizing acylanilides including bicalutamide and derivatives thereof |
ITMI20021392A1 (it) * | 2002-06-25 | 2003-12-29 | Nicox Sa | Forme farmaceutiche per la somministrazione orale di farmaci liquidi a temperatura ambiente dotate di migliore biodisponibilita' |
-
1998
- 1998-07-28 IT IT1998MI001743A patent/IT1303671B1/it active
-
1999
- 1999-07-20 AU AU52857/99A patent/AU770313C/en not_active Ceased
- 1999-07-20 EP EP99938300A patent/EP1098870B1/fr not_active Expired - Lifetime
- 1999-07-20 DE DE69927977T patent/DE69927977T2/de not_active Expired - Lifetime
- 1999-07-20 RU RU2001102262/04A patent/RU2254330C2/ru not_active IP Right Cessation
- 1999-07-20 CA CA2338854A patent/CA2338854C/fr not_active Expired - Fee Related
- 1999-07-20 JP JP2000562338A patent/JP4455760B2/ja not_active Expired - Fee Related
- 1999-07-20 US US09/743,808 patent/US6410791B1/en not_active Expired - Fee Related
- 1999-07-20 CN CNB998090425A patent/CN1264828C/zh not_active Expired - Fee Related
- 1999-07-20 AT AT99938300T patent/ATE307796T1/de active
- 1999-07-20 ES ES99938300T patent/ES2252958T3/es not_active Expired - Lifetime
- 1999-07-20 DK DK99938300T patent/DK1098870T3/da active
- 1999-07-20 KR KR1020017000803A patent/KR100687806B1/ko not_active IP Right Cessation
- 1999-07-20 IL IL14068599A patent/IL140685A0/xx not_active IP Right Cessation
- 1999-07-20 HU HU0102706A patent/HUP0102706A3/hu unknown
- 1999-07-20 WO PCT/EP1999/005171 patent/WO2000006531A2/fr not_active Application Discontinuation
- 1999-07-20 BR BR9912375-4A patent/BR9912375A/pt not_active Application Discontinuation
-
2001
- 2001-01-16 ZA ZA200100457A patent/ZA200100457B/en unknown
-
2002
- 2002-05-22 US US10/151,955 patent/US6828342B2/en not_active Expired - Fee Related
-
2003
- 2003-12-17 US US10/736,688 patent/US7122539B2/en not_active Expired - Fee Related
-
2004
- 2004-04-07 AU AU2004201457A patent/AU2004201457A1/en not_active Abandoned
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