JPH0132823B2 - - Google Patents
Info
- Publication number
- JPH0132823B2 JPH0132823B2 JP55045771A JP4577180A JPH0132823B2 JP H0132823 B2 JPH0132823 B2 JP H0132823B2 JP 55045771 A JP55045771 A JP 55045771A JP 4577180 A JP4577180 A JP 4577180A JP H0132823 B2 JPH0132823 B2 JP H0132823B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compounds
- compound
- formula
- pharmaceutically acceptable
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000000739 antihistaminic agent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- -1 tertiary-butyl Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 150000002148 esters Chemical class 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 230000001387 anti-histamine Effects 0.000 description 5
- 229940125715 antihistaminic agent Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 239000000043 antiallergic agent Substances 0.000 description 3
- 229940124630 bronchodilator Drugs 0.000 description 3
- 239000000168 bronchodilator agent Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 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
- 239000008120 corn starch Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- YYEROYLAYAVZNW-UHFFFAOYSA-N 2-methyl-2-phenylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC=C1 YYEROYLAYAVZNW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- UVZGOOXAARJPHD-UHFFFAOYSA-N butan-2-one;methanol Chemical compound OC.CCC(C)=O UVZGOOXAARJPHD-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000138 effect on histamine Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VGJYCLLSXQPXPR-UHFFFAOYSA-N 2-[3-(2,2,2-trifluoroacetyl)oxyphenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(OC(=O)C(F)(F)F)=C1 VGJYCLLSXQPXPR-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- XJMYBYYWKBKINH-UHFFFAOYSA-N 2-phenyl-2-(2,2,2-trifluoroacetyl)oxyacetic acid Chemical compound FC(F)(F)C(=O)OC(C(=O)O)C1=CC=CC=C1 XJMYBYYWKBKINH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- A61P11/08—Bronchodilators
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/028,813 US4254129A (en) | 1979-04-10 | 1979-04-10 | Piperidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55141469A JPS55141469A (en) | 1980-11-05 |
| JPH0132823B2 true JPH0132823B2 (US07321065-20080122-C00020.png) | 1989-07-10 |
Family
ID=21845568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4577180A Granted JPS55141469A (en) | 1979-04-10 | 1980-04-09 | Piperidine derivatives |
Country Status (19)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08500348A (ja) | 1992-08-03 | 1996-01-16 | セプラコア インコーポレーテッド | アレルギー疾患治療用のテルフェナジン代謝物及びその光学的に純粋な異性体 |
Families Citing this family (113)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR240018A1 (es) * | 1987-10-07 | 1990-01-31 | Merrell Pharma Inc | Procedimiento para preparar una composicion que comprende derivados de piperidinoalcanol. |
| CN1053570C (zh) | 1987-10-07 | 2000-06-21 | 默尔多药物公司 | 哌啶子基链烷醇的药用组合物-减充血剂复方的制备方法 |
| US4929605A (en) * | 1987-10-07 | 1990-05-29 | Merrell Dow Pharmaceuticals Inc. | Pharmaceutical composition for piperidinoalkanol derivatives |
| US4908372A (en) * | 1988-10-13 | 1990-03-13 | Merrell Dow Pharmaceuticals Inc. | Antihistaminic piperidinyl benzimidazoles |
| AR245888A1 (es) * | 1989-01-23 | 1994-03-30 | Merrell Pharma Inc | Procedimiento para la preparacion de una composicion farmaceutica liquida de derivados de piperidinoalcanol. |
| DE3917241A1 (de) * | 1989-05-26 | 1990-11-29 | Schaper & Bruemmer Gmbh | 4-(hydroxydiphenylmethyl)-1-piperidyl-phenylalkan-derivate |
| US5182097A (en) * | 1991-02-14 | 1993-01-26 | Virginia Commonwealth University | Formulations for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content |
| US5190029A (en) * | 1991-02-14 | 1993-03-02 | Virginia Commonwealth University | Formulation for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content |
| TW198008B (US07321065-20080122-C00020.png) * | 1991-04-08 | 1993-01-11 | Green Cross Corp | |
| HU211019B (en) * | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
| DE69330823T2 (de) * | 1992-02-13 | 2002-05-02 | Merrell Pharma Inc | Thiacyclische piperidinylderivate |
| EP0635004B1 (en) * | 1992-04-10 | 2002-07-17 | Merrell Pharmaceuticals Inc. | 4-diphenylmethyl piperidine derivatives and process for their preparation |
| US5631375A (en) * | 1992-04-10 | 1997-05-20 | Merrell Pharmaceuticals, Inc. | Process for piperidine derivatives |
| DE69320952T2 (de) | 1992-05-11 | 1999-05-27 | Merrell Pharma Inc | Verwendung von terfenadin-derivaten als antihistaminika in leberkranken patienten |
| US5654433A (en) * | 1993-01-26 | 1997-08-05 | Merrell Pharmaceuticals Inc. | Process for piperidine derivatives |
| US20020007068A1 (en) * | 1999-07-16 | 2002-01-17 | D'ambra Thomas E. | Piperidine derivatives and process for their production |
| ES2261871T3 (es) | 1993-06-24 | 2006-11-16 | Amr Technology, Inc. | Procedimiento para preparar compuestos utiles como intermediarios. |
| ES2190442T3 (es) * | 1993-06-25 | 2003-08-01 | Merrell Pharma Inc | Nuevos productos intermedios para la preparacion de derivados de 4-difenilmetil/difenilmetoxi piperidina antihistaminicos. |
| US6147216A (en) * | 1993-06-25 | 2000-11-14 | Merrell Pharmaceuticals Inc. | Intermediates useful for the preparation of antihistaminic piperidine derivatives |
| WO1995010278A1 (en) * | 1993-10-15 | 1995-04-20 | Hoechst Marion Roussel, Inc. | Treatment of allergic disorders with terfenadine carboxylate |
| PT725639E (pt) * | 1993-10-25 | 2001-02-28 | Merrell Pharma Inc | Composicao farmaceutica estavel de terfenadina e ibuprofeno |
| CA2189000C (en) * | 1994-05-16 | 2002-08-13 | Mitsuo Nakamura | Process and diastereomeric salts useful for the optical resolution of racemic .alpha.-[4-(1,1-dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol and derivative compounds |
| US20030045722A1 (en) * | 1994-05-18 | 2003-03-06 | Henton Daniel R. | Processes for preparing anhydrous and hydrate forms of antihistaminic piperidine derivatives, polymorphs and pseudomorphs thereof |
| EP2354125A1 (en) * | 1994-05-18 | 2011-08-10 | Aventisub II Inc. | Anhydrous and hydrate polymorphic forms of antihistaminic piperidine derivatives |
| CN101497581B (zh) * | 1994-05-18 | 2012-07-11 | 安万特萨博Ⅱ有限公司 | 抗组胺哌啶衍生物,其多晶形物和假同晶物的无水和水合物形式的制备方法 |
| ATE177095T1 (de) | 1994-08-25 | 1999-03-15 | Merrell Pharma Inc | Substituierte piperidine für die behandlung von allergischen krankheiten |
| KR100405116B1 (ko) * | 1995-02-28 | 2004-02-05 | 아벤티스 파마슈티칼스 인크. | 피페리디노알칸올화합물에대한약제학적조성물 |
| JPH11504650A (ja) * | 1995-05-08 | 1999-04-27 | ヘキスト・マリオン・ルセル・インコーポレイテツド | アルファ−（置換アルキルフェニル）−４−（ヒドロキシジフェニルメチル）−１−ピペリジンブタノール誘導体、その製造および抗ヒスタミン剤、抗アレルギー剤および気管支拡張剤としてのその使用 |
| US5574045A (en) * | 1995-06-06 | 1996-11-12 | Hoechst Marion Roussel, Inc. | Oral pharmaceutical composition of piperidinoalkanol compounds in solution form |
| US5906747A (en) * | 1995-11-13 | 1999-05-25 | Biosepra Inc. | Separation of molecules from dilute solutions using composite chromatography media having high dynamic sorptive capacity at high flow rates |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
| US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
| US6153754A (en) * | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
| US6201124B1 (en) | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| US5925761A (en) * | 1997-02-04 | 1999-07-20 | Sepracor Inc. | Synthesis of terfenadine and derivatives |
| ES2216191T3 (es) * | 1997-03-11 | 2004-10-16 | Aventis Pharmaceuticals Inc. | Procedimiento para preparar acido 4-(4-(hidroxidifenil)-1-piperidinil)-1-hidroxibutil)-alfa,alfa-dimetilfenilacetico y derivados fosforilados. |
| US6451815B1 (en) | 1997-08-14 | 2002-09-17 | Aventis Pharmaceuticals Inc. | Method of enhancing bioavailability of fexofenadine and its derivatives |
| SI0998272T1 (en) * | 1997-08-26 | 2003-12-31 | Aventis Pharmaceuticals Inc. | Pharmaceutical composition for combination of piperidinoalkanol-decongestant |
| ES2200260T3 (es) * | 1997-12-17 | 2004-03-01 | Aventis Pharma Deutschland Gmbh | Procedimiento para la alquilacion de derivados de alquil-o bencilciano en presencia de trialquilaminas o trialquifosfinas. |
| NZ520907A (en) * | 1997-12-23 | 2004-05-28 | Schering Corp | Composition for treating respiratory and skin diseases, comprising at least one leukotriene antagonist and at least one antihistamine |
| US6194431B1 (en) * | 1998-04-14 | 2001-02-27 | Paul D. Rubin | Methods and compositions using terfenadine metabolites in combination with leukotriene inhibitors |
| AU2007200674C1 (en) * | 1998-07-02 | 2011-02-24 | Aventisub Llc | Novel antihistaminic piperidine derivatives and intermediates for the preparation thereof |
| US6683094B2 (en) | 1998-07-02 | 2004-01-27 | Aventis Pharmaceuticals Inc. | Antihistaminic piperidine derivatives and intermediates for the preparation thereof |
| KR100707904B1 (ko) * | 1998-07-02 | 2007-04-16 | 아벤티스 파마슈티칼스 인크 | 항히스타민 피페리딘 유도체 및 이를 제조하기 위한 중간체 |
| US6930197B2 (en) | 1998-07-02 | 2005-08-16 | Aventis Pharmaceuticals Inc. | Antihistaminic piperidine derivatives and intermediates for the preparation thereof |
| GB9822170D0 (en) * | 1998-10-13 | 1998-12-02 | Danbioyst Uk Ltd | Novel formulations of fexofenadine |
| IN191492B (US07321065-20080122-C00020.png) * | 1999-05-25 | 2003-12-06 | Ranbaxy Lab Ltd | |
| US6613906B1 (en) * | 2000-06-06 | 2003-09-02 | Geneva Pharmaceuticals, Inc. | Crystal modification |
| US6613907B2 (en) | 2000-11-08 | 2003-09-02 | Amr Technology, Inc. | Process for the production of piperidine derivatives with microorganisms |
| CH695216A5 (de) * | 2001-02-23 | 2006-01-31 | Cilag Ag | Verfahren zur Herstellung eines nicht hydratisierten Salzes eines Piperidinderivats und eine so erhältliche neue kristalline Form eines solchen Salzes. |
| US20030021849A1 (en) * | 2001-04-09 | 2003-01-30 | Ben-Zion Dolitzky | Polymorphs of fexofenadine hydrochloride |
| KR20040012747A (ko) * | 2001-04-09 | 2004-02-11 | 테바 파마슈티컬 인더스트리즈 리미티드 | 펙소페나딘 염산염의 다형체 |
| BR0117054A (pt) * | 2001-06-18 | 2004-07-27 | Reddys Lab Ltd Dr | Formas cristalinas do ácido 4-[4-[4-hidroxidifenilmetil)-1-piperidinil]-1-hidroxibuti l]-alfa, alfa-dimetilbenzeno acético e seu cloridrato |
| US7700779B2 (en) | 2001-06-18 | 2010-04-20 | Dr. Reddy's Laboratories Limited | Crystalline forms of fexofenadine and its hydrochloride |
| US20030158227A1 (en) * | 2001-11-08 | 2003-08-21 | Barnaba Krochmal | Polymorphs of fexofenadine base |
| AU2002357701A1 (en) * | 2001-11-08 | 2003-05-19 | Teva Pharmaceutical Industries Ltd. | Polymorphs of fexofenadine base |
| US6723348B2 (en) * | 2001-11-16 | 2004-04-20 | Ethypharm | Orodispersible tablets containing fexofenadine |
| JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
| US20040044038A1 (en) * | 2002-06-10 | 2004-03-04 | Barnaba Krochmal | Polymorphic form XVI of fexofenadine hydrochloride |
| EP1575893A1 (en) * | 2002-12-16 | 2005-09-21 | Ranbaxy Laboratories Limited | Process for the preparation of fexofenadine |
| CA2514610A1 (en) * | 2003-01-31 | 2004-08-12 | Ranbaxy Laboratories Limited | Process for the preparation of fexofenadine |
| US20050026890A1 (en) * | 2003-07-31 | 2005-02-03 | Robinson Cynthia B. | Combination of dehydroepiandrosterone or dehydroepiandrosterone-sulfate with an antihistamine for treatment of asthma or chronic obstructive pulmonary disease |
| US20050065183A1 (en) * | 2003-07-31 | 2005-03-24 | Indranil Nandi | Fexofenadine composition and process for preparing |
| GB0319935D0 (en) * | 2003-08-26 | 2003-09-24 | Cipla Ltd | Polymorphs |
| TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
| KR20070007196A (ko) * | 2004-04-26 | 2007-01-12 | 테바 파마슈티컬 인더스트리즈 리미티드 | 펙소페나딘 히드로클로라이드의 결정형 및 이의 제조 방법 |
| WO2006008567A1 (en) * | 2004-06-18 | 2006-01-26 | Wockhardt Limited | Pharmaceutical compositions for piperidinoalkanol compounds |
| ITMI20041568A1 (it) * | 2004-07-30 | 2004-10-30 | Dipharma Spa | "polimorfi di fexofenadina base" |
| US7498345B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
| US7498443B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of carebastine |
| US20060148851A1 (en) * | 2004-09-28 | 2006-07-06 | Shlomit Wizel | Fexofenadine crystal form and processes for its preparation thereof |
| NZ555501A (en) * | 2004-11-24 | 2010-01-29 | Medpointe Healthcare Inc | Compositions comprising azelastine and methods of use thereof |
| US8758816B2 (en) * | 2004-11-24 | 2014-06-24 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US20070020330A1 (en) | 2004-11-24 | 2007-01-25 | Medpointe Healthcare Inc. | Compositions comprising azelastine and methods of use thereof |
| JP2008120684A (ja) * | 2005-03-07 | 2008-05-29 | Kumamoto Univ | 抗アレルギー薬 |
| JP5133244B2 (ja) * | 2005-08-05 | 2013-01-30 | ルピン・リミテッド | フェキソフェナジンの経口用医薬懸濁組成物 |
| US20080292584A1 (en) * | 2005-10-14 | 2008-11-27 | Mutual Pharmaceutical Company, Inc. | Metaxalone products, method of manufacture, and method of use |
| US20070088065A1 (en) * | 2005-10-14 | 2007-04-19 | Jie Du | Metaxalone products, method of manufacture, and method of use |
| WO2007049303A2 (en) * | 2005-10-28 | 2007-05-03 | Ind-Swift Laboratories Limited | An improved process for the preparation of highly pure fexofenadine |
| EP2218442A1 (en) | 2005-11-09 | 2010-08-18 | CombinatoRx, Inc. | Methods, compositions, and kits for the treatment of ophthalmic disorders |
| DOP2006000274A (es) * | 2005-12-14 | 2007-10-15 | Sanofi Aventis Us Llc | Formulación de suspensión de fexofenadina |
| CN100443470C (zh) * | 2006-07-21 | 2008-12-17 | 杭州保灵有限公司 | 一种依巴斯汀的制备方法 |
| ITMI20061492A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
| ITMI20061491A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
| US20080161324A1 (en) * | 2006-09-14 | 2008-07-03 | Johansen Lisa M | Compositions and methods for treatment of viral diseases |
| MX2009011068A (es) | 2007-04-13 | 2010-01-13 | Southern Res Inst | Agentes anti-angiogenicos y metodos de utilizacion. |
| ITMI20070987A1 (it) * | 2007-05-16 | 2008-11-17 | Dipharma Francis Srl | Procedimento per la preparazione di composti chetonici |
| US20090076080A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched fexofenadine |
| EP2105134A1 (en) | 2008-03-24 | 2009-09-30 | Ranbaxy Laboratories Limited | Stable amorphous fexofenadine hydrochloride |
| WO2009158144A1 (en) * | 2008-05-30 | 2009-12-30 | Fairfield Clinical Trials Llc | Method and composition for dermatoses |
| WO2010021681A2 (en) * | 2008-08-18 | 2010-02-25 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
| CN101585805B (zh) * | 2009-06-06 | 2011-07-06 | 浙江大学宁波理工学院 | 一种抗过敏药物非索非那定盐酸盐的制备方法 |
| EP2289867A3 (en) | 2009-08-19 | 2012-04-25 | Jubilant Organosys Limited | A process for producing 4-(4-halo-1-oxybutyl)-alpha,alpha-dimethylbenzene acetic acid or alkyl esters thereof |
| CN101671292B (zh) * | 2009-10-10 | 2011-09-07 | 浙江大学宁波理工学院 | 盐酸非索非那定的合成方法 |
| US20110130711A1 (en) * | 2009-11-19 | 2011-06-02 | Follica, Inc. | Hair growth treatment |
| EP2371817A1 (en) * | 2010-04-01 | 2011-10-05 | Arevipharma GmbH | Process for the preparation of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone and acid addition salts thereof |
| WO2011158262A1 (en) | 2010-06-15 | 2011-12-22 | Chemelectiva S.R.L. | Polymorphic form of fexofenadine hydrochloride, intermediates and process for its preparation |
| EP2714624B1 (en) | 2011-05-23 | 2017-12-27 | Sanofi | Process for the preparation of deuterated compounds containing n-alkyl groups |
| TW201318624A (zh) | 2011-09-29 | 2013-05-16 | Shionogi & Co | 包含ｐｇｄ２拮抗劑及組織胺拮抗劑之過敏性鼻炎治療用醫藥 |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| CN102659667B (zh) * | 2012-04-20 | 2013-08-14 | 浙江启明药业有限公司 | 一种非索非那定关键中间体的合成方法 |
| CN103333100B (zh) * | 2013-06-06 | 2016-04-06 | 池州东升药业有限公司 | 一种盐酸非索非那定的合成工艺 |
| ITMI20131652A1 (it) | 2013-10-07 | 2015-04-08 | Dipharma Francis Srl | Procedimento per la purificazione di derivati dell'acido 2-fenil-2-metil-propanoico |
| CN104557671B (zh) * | 2013-10-10 | 2018-04-13 | 池州东升药业有限公司 | 一种非索非那定及中间体的合成方法 |
| EP2949321A1 (en) | 2014-05-26 | 2015-12-02 | Sanovel Ilac Sanayi ve Ticaret A.S. | Multilayer formulations of fexofenadine and montelukast |
| PL3247699T3 (pl) | 2015-01-22 | 2019-11-29 | Sanofi Aventis Deutschland | Sposób wytwarzania 2-[4-(cyklopropanokarbonylo)fenylo]-2-metylo-propanonitrylu |
| EP3365327B1 (en) | 2015-10-22 | 2019-11-20 | Sanofi-Aventis Deutschland GmbH | Process for the preparation of fexofenadine and of intermediates used therein |
| GB202212656D0 (en) | 2022-08-31 | 2022-10-12 | Novumgen Ltd | An orodispersible tablet of fecofenadine and it process of preparation |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885578A (US07321065-20080122-C00020.png) * | 1972-01-28 | 1973-11-13 | ||
| JPS50108266A (US07321065-20080122-C00020.png) * | 1974-02-08 | 1975-08-26 | ||
| JPS50108265A (US07321065-20080122-C00020.png) * | 1974-02-08 | 1975-08-26 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1242169A (en) * | 1969-04-09 | 1971-08-11 | Ucb Sa | Piperidine derivatives |
| US3965257A (en) * | 1972-01-28 | 1976-06-22 | Richardson-Merrell Inc. | Compositions and methods for the treatment of the symptoms of histamine induced allergic reactions |
| BE794596A (fr) * | 1972-01-28 | 1973-05-16 | Richardson Merrell Inc | Piperidinoalcanone-oximes substituees et leur procede de preparation |
| BE794598A (fr) * | 1972-01-28 | 1973-05-16 | Richardson Merrell Inc | Nouveaux derives olefiniques de piperidines substituees en 4 et leur procede de preparation |
| US3878217A (en) * | 1972-01-28 | 1975-04-15 | Richardson Merrell Inc | Alpha-aryl-4-substituted piperidinoalkanol derivatives |
| US3806526A (en) * | 1972-01-28 | 1974-04-23 | Richardson Merrell Inc | 1-aroylalkyl-4-diphenylmethyl piperidines |
| US3946022A (en) * | 1974-03-04 | 1976-03-23 | Richardson-Merrell Inc. | Piperidine derivatives |
| US3922276A (en) * | 1974-12-11 | 1975-11-25 | Robins Co Inc A H | 1-Substituted-4-benzylidenepiperidines |
| US3956296A (en) * | 1974-12-11 | 1976-05-11 | A. H. Robins Company, Incorporated | 1-Substituted-4-benzylpiperidines |
-
1979
- 1979-04-10 US US06/028,813 patent/US4254129A/en not_active Expired - Lifetime
-
1980
- 1980-01-18 CA CA344,020A patent/CA1123438A/en not_active Expired
- 1980-01-18 NZ NZ192653A patent/NZ192653A/xx unknown
- 1980-01-18 IL IL59158A patent/IL59158A/xx unknown
- 1980-01-21 ZA ZA00800332A patent/ZA80332B/xx unknown
- 1980-01-29 AU AU55016/80A patent/AU531146B2/en not_active Expired
- 1980-02-07 NL NL8000754A patent/NL190580C/xx not_active IP Right Cessation
- 1980-02-28 DE DE19803007498 patent/DE3007498A1/de active Granted
- 1980-03-05 CH CH174180A patent/CH643245A5/de not_active IP Right Cessation
- 1980-03-17 AT AT0144880A patent/AT376208B/de not_active IP Right Cessation
- 1980-03-24 IT IT48245/80A patent/IT1143960B/it active Protection Beyond IP Right Term
- 1980-03-26 ES ES489934A patent/ES8103735A1/es not_active Expired
- 1980-03-27 DK DK132980A patent/DK153709C/da not_active IP Right Cessation
- 1980-03-28 PH PH23831A patent/PH17023A/en unknown
- 1980-04-08 SE SE8002634A patent/SE448726B/sv not_active IP Right Cessation
- 1980-04-09 NO NO801014A patent/NO154521C/no unknown
- 1980-04-09 BE BE0/200161A patent/BE882703A/fr not_active IP Right Cessation
- 1980-04-09 JP JP4577180A patent/JPS55141469A/ja active Granted
- 1980-04-09 FR FR8007992A patent/FR2453854A1/fr active Granted
-
1998
- 1998-04-08 NL NL980013C patent/NL980013I2/nl unknown
- 1998-05-29 NO NO1998017C patent/NO1998017I1/no unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885578A (US07321065-20080122-C00020.png) * | 1972-01-28 | 1973-11-13 | ||
| JPS50108266A (US07321065-20080122-C00020.png) * | 1974-02-08 | 1975-08-26 | ||
| JPS50108265A (US07321065-20080122-C00020.png) * | 1974-02-08 | 1975-08-26 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08500348A (ja) | 1992-08-03 | 1996-01-16 | セプラコア インコーポレーテッド | アレルギー疾患治療用のテルフェナジン代謝物及びその光学的に純粋な異性体 |
| JP2000086516A (ja) * | 1992-08-03 | 2000-03-28 | Sepracor Inc | テルフェナジンカルボキシレ―トの使用方法 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0132823B2 (US07321065-20080122-C00020.png) | ||
| US4285957A (en) | 1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof | |
| US4285958A (en) | 1-Piperidine-alkylene ketones, pharmaceutical compositions thereof and method of use thereof | |
| US4254130A (en) | Piperidine derivatives | |
| US3878217A (en) | Alpha-aryl-4-substituted piperidinoalkanol derivatives | |
| KR910009937B1 (ko) | 피페리딘 유도체 및 그의 제법 | |
| JP3034047B2 (ja) | ピペリジン誘導体及びそれらの製造法 | |
| JP4865113B2 (ja) | ピペリジン誘導体の製法 | |
| JP2002308850A (ja) | 形態ｉｉの抗ヒスタミン性ピペリジン誘導体およびその製造方法 | |
| JP2009019058A (ja) | ピペリジン誘導体の製法 | |
| HUT72747A (en) | Process for producing thiazolylvinylphenyl-compounds and pharmaceutical compositions containing them | |
| JP2007503423A (ja) | フェキソフェナジンの結晶多形、及びそれらを製造する方法 | |
| NO144455B (no) | Fremgangsmaate ved fremstilling av terapeutisk aktive nye piperidinderivater | |
| US3852455A (en) | 4-{8 4({60 hydroxybenzyl)piperidino{9 -4-fluorobutyrophenone derivatives as tranquilizers | |
| JPH09505274A (ja) | 抗炎症剤、抗アレルギー剤および免疫変調剤としての４−アルキルアミノ−１−フェノキシアルキルピペリジン | |
| US4180583A (en) | Olefinic 4-substituted piperidino derivatives as therapeutics | |
| US4029790A (en) | 1-Benzoyl-2 or 4 [2-(4-phenyl-piperazino)-ethyl]-piperidines | |
| JPH02138174A (ja) | １，４−ジ置換ピペジニル化合物類 | |
| US4248877A (en) | Organic compounds | |
| PL173775B1 (pl) | Arylideno-1-azacykloalkany i aryloalkilo-1-azacykloalkany, ich sole oraz sposób ich wytwarzania | |
| WO1997009983A1 (en) | Piperidine derivatives and processes for their production | |
| JPS6341390B2 (US07321065-20080122-C00020.png) | ||
| US4178377A (en) | (4-Hydroxy-4-piperidyl)-alkanoic acid amides | |
| GB2048258A (en) | Piperidine Derivatives | |
| US5183896A (en) | Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime |
