SK12682003A3 - Prípravky obsahujúce imidazotriazinón na nazálnu aplikáciu - Google Patents

Prípravky obsahujúce imidazotriazinón na nazálnu aplikáciu Download PDF

Info

Publication number: SK12682003A3
Authority: SK; Slovakia
Prior art keywords: group; hydrochloride; carbon atoms; alkyl; optionally
Prior art date: 2001-04-12

Application number

SK1268-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Serno

Andreas Ohm

Wolfgang Barth

Richard-Josef Bauer

Hans-Martin Siefert

Dieter Zimmer

Original Assignee

Bayer Aktiengesellschaft

Priority date (The priority date 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 date listed.)

2001-04-12

Filing date

2002-04-03

Publication date

2004-03-02

2002-04-03 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

2004-03-02 Publication of SK12682003A3 publication Critical patent/SK12682003A3/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 74
IJYHVZICHKCLMQ-UHFFFAOYSA-N imidazo[4,5-d]triazin-4-one Chemical compound O=C1N=NN=C2N=CN=C12 IJYHVZICHKCLMQ-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 22
229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 46
239000003589 local anesthetic agent Substances 0.000 claims description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 26
238000009472 formulation Methods 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 19
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 16
-1 hydroxy, carboxyl Chemical group 0.000 claims description 16
229960004194 lidocaine Drugs 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 claims description 11
239000003112 inhibitor Substances 0.000 claims description 11
239000000843 powder Substances 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
229940097496 nasal spray Drugs 0.000 claims description 10
239000007922 nasal spray Substances 0.000 claims description 10
229960003502 oxybuprocaine Drugs 0.000 claims description 10
CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 claims description 10
150000004677 hydrates Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
239000001301 oxygen Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000003755 preservative agent Substances 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
229910052717 sulfur Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
239000003963 antioxidant agent Substances 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000004094 surface-active agent Substances 0.000 claims description 6
229920001363 Polidocanol Polymers 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000000796 flavoring agent Substances 0.000 claims description 5
229960002226 polidocanol Drugs 0.000 claims description 5
ONJQDTZCDSESIW-UHFFFAOYSA-N polidocanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ONJQDTZCDSESIW-UHFFFAOYSA-N 0.000 claims description 5
208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
229960005274 benzocaine Drugs 0.000 claims description 4
229960001290 butanilicaine Drugs 0.000 claims description 4
VWYQKFLLGRBICZ-UHFFFAOYSA-N butanilicaine Chemical compound CCCCNCC(=O)NC1=C(C)C=CC=C1Cl VWYQKFLLGRBICZ-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
CVHGCWVMTZWGAY-UHFFFAOYSA-N fomocaine Chemical compound C=1C=C(COC=2C=CC=CC=2)C=CC=1CCCN1CCOCC1 CVHGCWVMTZWGAY-UHFFFAOYSA-N 0.000 claims description 4
229950003051 fomocaine Drugs 0.000 claims description 4
235000013355 food flavoring agent Nutrition 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000003906 humectant Substances 0.000 claims description 4
201000001881 impotence Diseases 0.000 claims description 4
229960004393 lidocaine hydrochloride Drugs 0.000 claims description 4
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
229960004919 procaine Drugs 0.000 claims description 4
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 4
229960002372 tetracaine Drugs 0.000 claims description 4
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 4
ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 claims description 3
XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
239000000872 buffer Substances 0.000 claims description 3
239000003623 enhancer Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
229960005038 quinisocaine Drugs 0.000 claims description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
ZXSGQNYQJIUMQN-UHFFFAOYSA-N 3-(2-methylpiperidin-1-ium-1-yl)propyl benzoate;chloride Chemical compound Cl.CC1CCCCN1CCCOC(=O)C1=CC=CC=C1 ZXSGQNYQJIUMQN-UHFFFAOYSA-N 0.000 claims description 2
LMWQQUMMGGIGJQ-UHFFFAOYSA-N Etidocaine hydrochloride Chemical compound [Cl-].CCC[NH+](CC)C(CC)C(=O)NC1=C(C)C=CC=C1C LMWQQUMMGGIGJQ-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
YQKAVWCGQQXBGW-UHFFFAOYSA-N Piperocaine Chemical compound CC1CCCCN1CCCOC(=O)C1=CC=CC=C1 YQKAVWCGQQXBGW-UHFFFAOYSA-N 0.000 claims description 2
PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
229960001050 bupivacaine hydrochloride Drugs 0.000 claims description 2
229960000400 butamben Drugs 0.000 claims description 2
IUWVALYLNVXWKX-UHFFFAOYSA-N butamben Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1 IUWVALYLNVXWKX-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229960000385 dyclonine Drugs 0.000 claims description 2
BZEWSEKUUPWQDQ-UHFFFAOYSA-N dyclonine Chemical compound C1=CC(OCCCC)=CC=C1C(=O)CCN1CCCCC1 BZEWSEKUUPWQDQ-UHFFFAOYSA-N 0.000 claims description 2
KNZADIMHVBBPOA-UHFFFAOYSA-N dyclonine hydrochloride Chemical compound [Cl-].C1=CC(OCCCC)=CC=C1C(=O)CC[NH+]1CCCCC1 KNZADIMHVBBPOA-UHFFFAOYSA-N 0.000 claims description 2
229960003462 dyclonine hydrochloride Drugs 0.000 claims description 2
229960001804 etidocaine hydrochloride Drugs 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229960002409 mepivacaine Drugs 0.000 claims description 2
INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
CGNCROPFTZJYCW-UHFFFAOYSA-N methyl 5-[[2-(diethylamino)acetyl]amino]-2-hydroxybenzoate Chemical compound CCN(CC)CC(=O)NC1=CC=C(O)C(C(=O)OC)=C1 CGNCROPFTZJYCW-UHFFFAOYSA-N 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229960001045 piperocaine Drugs 0.000 claims description 2
229960001896 pramocaine Drugs 0.000 claims description 2
DQKXQSGTHWVTAD-UHFFFAOYSA-N pramocaine Chemical compound C1=CC(OCCCC)=CC=C1OCCCN1CCOCC1 DQKXQSGTHWVTAD-UHFFFAOYSA-N 0.000 claims description 2
229960005094 prilocaine hydrochloride Drugs 0.000 claims description 2
BJPJNTKRKALCPP-UHFFFAOYSA-N prilocaine hydrochloride Chemical compound [Cl-].CCC[NH2+]C(C)C(=O)NC1=CC=CC=C1C BJPJNTKRKALCPP-UHFFFAOYSA-N 0.000 claims description 2
229960001549 ropivacaine Drugs 0.000 claims description 2
JCQBWMAWTUBARI-UHFFFAOYSA-N tert-butyl 3-ethenylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(C=C)C1 JCQBWMAWTUBARI-UHFFFAOYSA-N 0.000 claims description 2
229960002494 tetracaine hydrochloride Drugs 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
239000004606 Fillers/Extenders Substances 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
AFFQPCNKJKMLTE-UHFFFAOYSA-N 2-[2-hydroxyethyl-[2-[methyl-(2-methyl-1-phenylpropan-2-yl)amino]-2-oxoethyl]amino]-n-methyl-n-(2-methyl-1-phenylpropan-2-yl)acetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CC(C)(C)N(C)C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC1=CC=CC=C1 AFFQPCNKJKMLTE-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
FTLDJPRFCGDUFH-UHFFFAOYSA-N Oxethazaine Chemical compound C=1C=CC=CC=1CC(C)(C)N(C)C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC1=CC=CC=C1 FTLDJPRFCGDUFH-UHFFFAOYSA-N 0.000 claims 1
235000008331 Pinus X rigitaeda Nutrition 0.000 claims 1
235000011613 Pinus brutia Nutrition 0.000 claims 1
241000018646 Pinus brutia Species 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
235000019634 flavors Nutrition 0.000 claims 1
229960000986 oxetacaine Drugs 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
STHAHFPLLHRRRO-UHFFFAOYSA-N propipocaine Chemical compound C1=CC(OCCC)=CC=C1C(=O)CCN1CCCCC1 STHAHFPLLHRRRO-UHFFFAOYSA-N 0.000 claims 1
229950011219 propipocaine Drugs 0.000 claims 1
239000000080 wetting agent Substances 0.000 claims 1
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 abstract description 2
230000003444 anaesthetic effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 29
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
239000004743 Polypropylene Substances 0.000 description 22
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
229960005015 local anesthetics Drugs 0.000 description 10
229960002381 vardenafil Drugs 0.000 description 10
210000001331 nose Anatomy 0.000 description 9
230000000052 comparative effect Effects 0.000 description 8
229940098779 methanesulfonic acid Drugs 0.000 description 8
239000008213 purified water Substances 0.000 description 8
239000004480 active ingredient Substances 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
229960001747 cinchocaine Drugs 0.000 description 6
PUFQVTATUTYEAL-UHFFFAOYSA-N cinchocaine Chemical compound C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCCN(CC)CC)=C21 PUFQVTATUTYEAL-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
230000007794 irritation Effects 0.000 description 5
210000002850 nasal mucosa Anatomy 0.000 description 5
206010002091 Anaesthesia Diseases 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
230000037005 anaesthesia Effects 0.000 description 4
235000006708 antioxidants Nutrition 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000000304 vasodilatating effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
206010028735 Nasal congestion Diseases 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
230000037396 body weight 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
229930195733 hydrocarbon Natural products 0.000 description 3
230000000622 irritating effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
PRGUDWLMFLCODA-UHFFFAOYSA-N oxybuprocaine hydrochloride Chemical compound [Cl-].CCCCOC1=CC(C(=O)OCC[NH+](CC)CC)=CC=C1N PRGUDWLMFLCODA-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
FBCDRHDULQYRTB-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-4-one;trihydrate;hydrochloride Chemical group O.O.O.Cl.CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 FBCDRHDULQYRTB-UHFFFAOYSA-N 0.000 description 2
UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 2
WEWNUXJEVSROFW-UHFFFAOYSA-N 5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCCC1=NN(C)C(C(N=2)=O)=C1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 WEWNUXJEVSROFW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
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229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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BNRNXUUZRGQAQC-UHFFFAOYSA-N Sildenafil Natural products CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 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
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
230000007803 itching Effects 0.000 description 1
YNQQEYBLVYAWNX-WLHGVMLRSA-N ketotifen fumarate Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 YNQQEYBLVYAWNX-WLHGVMLRSA-N 0.000 description 1
229960003630 ketotifen fumarate Drugs 0.000 description 1
230000004317 lacrimation Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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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
230000010534 mechanism of action Effects 0.000 description 1
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239000012528 membrane Substances 0.000 description 1
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RETIMRUQNCDCQB-UHFFFAOYSA-N mepivacaine hydrochloride Chemical compound Cl.CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C RETIMRUQNCDCQB-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
210000003928 nasal cavity Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
229940074355 nitric acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
210000000929 nociceptor Anatomy 0.000 description 1
229940066429 octoxynol Drugs 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000018052 penile erection Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
229940067631 phospholipid Drugs 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940099429 polyoxyl 40 stearate Drugs 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940093932 potassium hydroxide Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
125000004673 propylcarbonyl group Chemical group 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 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
229960001813 ropivacaine hydrochloride Drugs 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
230000035807 sensation Effects 0.000 description 1
239000004003 serotonin 1D agonist Substances 0.000 description 1
229960002639 sildenafil citrate Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
229940001607 sodium bisulfite Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229940083608 sodium hydroxide Drugs 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229960004906 thiomersal Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
QQJLHRRUATVHED-UHFFFAOYSA-N tramazoline Chemical compound N1CCN=C1NC1=CC=CC2=C1CCCC2 QQJLHRRUATVHED-UHFFFAOYSA-N 0.000 description 1
229960001262 tramazoline Drugs 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
229940045136 urea Drugs 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
229940117960 vanillin Drugs 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229940094720 viagra Drugs 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Otolaryngology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Anesthesiology (AREA)
Gynecology & Obstetrics (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1268-2003A 2001-04-12 2002-04-03 Prípravky obsahujúce imidazotriazinón na nazálnu aplikáciu SK12682003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10118306A DE10118306A1 (de)	2001-04-12	2001-04-12	Imidazotriazinonhaltige Zusammensetzungen zur nasalen Applikation
PCT/EP2002/003663 WO2002083674A2 (de)	2001-04-12	2002-04-03	Imidazotriazinonhaltige zusammensetzungen zur nasalen applikation

Publications (1)

Publication Number	Publication Date
SK12682003A3 true SK12682003A3 (sk)	2004-03-02

Family

ID=7681379

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1268-2003A SK12682003A3 (sk)	2001-04-12	2002-04-03	Prípravky obsahujúce imidazotriazinón na nazálnu aplikáciu

Country Status (25)

Country	Link
US (2)	US6740306B2 (no)
EP (1)	EP1381368A2 (no)
JP (1)	JP2004525968A (no)
KR (1)	KR20030087072A (no)
CN (1)	CN1537004A (no)
AR (1)	AR035821A1 (no)
BG (1)	BG108245A (no)
BR (1)	BR0208813A (no)
CA (1)	CA2443639A1 (no)
CZ (1)	CZ20032752A3 (no)
DE (1)	DE10118306A1 (no)
DO (1)	DOP2002000373A (no)
EC (1)	ECSP034795A (no)
EE (1)	EE200300501A (no)
GT (1)	GT200200070A (no)
HU (1)	HUP0303877A3 (no)
IL (1)	IL158255A0 (no)
MX (1)	MXPA03009314A (no)
NO (1)	NO20034556L (no)
PE (1)	PE20021035A1 (no)
PL (1)	PL363033A1 (no)
RU (1)	RU2003133143A (no)
SK (1)	SK12682003A3 (no)
UY (1)	UY27256A1 (no)
WO (1)	WO2002083674A2 (no)

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PL363679A1 (en) *	2001-05-09	2004-11-29	Bayer Healthcare Ag	Novel use of 2-phenyl-substituted imidazotriazinones
DE102004023069A1 (de) *	2004-05-11	2005-12-08	Bayer Healthcare Ag	Neue Darreichungsformen des PDE 5-Inhibitors Vardenafil
ZA200704869B (en) *	2004-12-23	2009-02-25	Roxro Pharma Inc	Therapeutic compositions for intranasal administration of ketorolac
DE102005001989A1 (de) *	2005-01-15	2006-07-20	Bayer Healthcare Ag	Intravenöse Formulierungen von PDE-Inhibitoren
DE102005009240A1 (de) *	2005-03-01	2006-09-07	Bayer Healthcare Ag	Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften
DE102005009241A1 (de) *	2005-03-01	2006-09-07	Bayer Healthcare Ag	Arzneiformen mit kontrollierter Bioverfügbarkeit
US20070031349A1 (en) *	2005-06-23	2007-02-08	David Monteith	Rapidly absorbing oral formulations of PDE 5 inhibitors
CA2623657A1 (en) *	2005-09-29	2007-04-12	Bayer Healthcare Ag	Pde inhibitors and combinations thereof for the treatment of urological disorders
EP2167057A1 (en) *	2007-06-13	2010-03-31	Bayer HealthCare AG	Pde inhibitors for the treatment of hearing impairment
CN102137656A (zh) *	2008-06-13	2011-07-27	罗克斯罗制药公司	用于鼻内投予的酮咯酸医药调配物
US8277781B2 (en) *	2009-03-13	2012-10-02	Luitpold Pharmaceuticals, Inc.	Device for intranasal administration
US8551454B2 (en) *	2009-03-13	2013-10-08	Luitpold Pharmaceuticals, Inc.	Device for intranasal administration
WO2017168174A1 (en)	2016-04-02	2017-10-05	N4 Pharma Uk Limited	New pharmaceutical forms of sildenafil
WO2020006606A1 (en) *	2018-07-05	2020-01-09	Helium 3 Resources Pty Ltd	A pharmaceutical composition and method of use of same
SE542968C2 (en) *	2018-10-26	2020-09-22	Lindahl Anders	Treatment of osteoarthritis
IL298432A (en) *	2020-05-26	2023-01-01	Strategic Drug Solutions Inc	Formulations and methods for treating erectile dysfunction

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US4602099A (en) *	1973-04-02	1986-07-22	Merrell Dow Pharmaceuticals Inc.	Antirhinovirus agents
GB9013750D0 (en)	1990-06-20	1990-08-08	Pfizer Ltd	Therapeutic agents
GB9301192D0 (en)	1993-06-09	1993-06-09	Trott Francis W	Flower shaped mechanised table
GB9514465D0 (en)	1995-07-14	1995-09-13	Glaxo Lab Sa	Chemical compounds
GB9514473D0 (en)	1995-07-14	1995-09-13	Glaxo Lab Sa	Chemical compounds
EP0985671B1 (en)	1996-05-31	2003-04-02	Mochida Pharmaceutical Co., Ltd.	PYRIDOCARBAZOLE DERIVATIVES HAVING cGMP-PDE INHIBITORY EFFECT
GB2315673A (en) *	1996-08-01	1998-02-11	Merck & Co Inc	Treatment of migraine
CN1309561A (zh) *	1997-05-29	2001-08-22	持田制药株式会社	勃起机能障碍治疗剂
JP2001517628A (ja)	1997-09-23	2001-10-09	イーライ・リリー・アンド・カンパニー	注意欠陥／多動障害の治療法
TR200001338T2 (tr)	1997-11-12	2000-08-21	Bayer Aktiengesellschaft	2-Fenil-ikameli imidazotriazinonlar
TWI223598B (en) *	1998-06-22	2004-11-11	Pfizer Ireland Pharmaceuticals	An intranasal pharmaceutical composition for the treatment of male erectile dysfunction or female sexual disorders, an intranasal delivery system or device and sildenafil mesylate
WO2000000199A1 (en) *	1998-06-26	2000-01-06	Nastech Pharmaceutical Company, Inc.	Nasal delivery of sildenafil citrate
WO2000035434A2 (en) *	1998-12-14	2000-06-22	Cellegy Pharmaceuticals, Inc.	Compositions and methods for the treatment of anorectal disorders

2001
- 2001-04-12 DE DE10118306A patent/DE10118306A1/de not_active Withdrawn
2002
- 2002-04-03 IL IL15825502A patent/IL158255A0/xx unknown
- 2002-04-03 HU HU0303877A patent/HUP0303877A3/hu unknown
- 2002-04-03 EE EEP200300501A patent/EE200300501A/xx unknown
- 2002-04-03 EP EP02732548A patent/EP1381368A2/de not_active Withdrawn
- 2002-04-03 WO PCT/EP2002/003663 patent/WO2002083674A2/de not_active Ceased
- 2002-04-03 CA CA002443639A patent/CA2443639A1/en not_active Abandoned
- 2002-04-03 SK SK1268-2003A patent/SK12682003A3/sk unknown
- 2002-04-03 CZ CZ20032752A patent/CZ20032752A3/cs unknown
- 2002-04-03 JP JP2002581429A patent/JP2004525968A/ja active Pending
- 2002-04-03 BR BR0208813-4A patent/BR0208813A/pt not_active Application Discontinuation
- 2002-04-03 MX MXPA03009314A patent/MXPA03009314A/es unknown
- 2002-04-03 CN CNA028114574A patent/CN1537004A/zh active Pending
- 2002-04-03 PL PL02363033A patent/PL363033A1/xx not_active Application Discontinuation
- 2002-04-03 KR KR10-2003-7013280A patent/KR20030087072A/ko not_active Withdrawn
- 2002-04-03 RU RU2003133143/15A patent/RU2003133143A/ru not_active Application Discontinuation
- 2002-04-04 DO DO2002000373A patent/DOP2002000373A/es unknown
- 2002-04-10 AR ARP020101322A patent/AR035821A1/es not_active Application Discontinuation
- 2002-04-11 PE PE2002000303A patent/PE20021035A1/es not_active Application Discontinuation
- 2002-04-11 UY UY27256A patent/UY27256A1/es not_active Application Discontinuation
- 2002-04-11 US US10/122,694 patent/US6740306B2/en not_active Expired - Fee Related
- 2002-04-11 GT GT200200070A patent/GT200200070A/es unknown
2003
- 2003-10-08 EC EC2003004795A patent/ECSP034795A/es unknown
- 2003-10-09 BG BG108245A patent/BG108245A/xx unknown
- 2003-10-10 NO NO20034556A patent/NO20034556L/no not_active Application Discontinuation
2004
- 2004-03-30 US US10/813,801 patent/US20040248891A1/en not_active Abandoned

Also Published As

Publication number	Publication date
UY27256A1 (es)	2002-11-29
WO2002083674A2 (de)	2002-10-24
AR035821A1 (es)	2004-07-14
HUP0303877A2 (hu)	2004-03-29
DOP2002000373A (es)	2002-11-30
NO20034556D0 (no)	2003-10-10
IL158255A0 (en)	2004-05-12
CA2443639A1 (en)	2002-10-24
BG108245A (en)	2005-01-31
RU2003133143A (ru)	2005-04-10
US20030022894A1 (en)	2003-01-30
US20040248891A1 (en)	2004-12-09
NO20034556L (no)	2003-12-10
PE20021035A1 (es)	2002-11-29
MXPA03009314A (es)	2004-03-10
JP2004525968A (ja)	2004-08-26
GT200200070A (es)	2003-01-31
CN1537004A (zh)	2004-10-13
ECSP034795A (es)	2003-12-01
HUP0303877A3 (en)	2005-05-30
EE200300501A (et)	2003-12-15
BR0208813A (pt)	2004-03-09
CZ20032752A3 (cs)	2004-01-14
KR20030087072A (ko)	2003-11-12
US6740306B2 (en)	2004-05-25
PL363033A1 (en)	2004-11-15
EP1381368A2 (de)	2004-01-21
WO2002083674A3 (de)	2003-01-09
DE10118306A1 (de)	2002-10-17

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