OA12300A - Carbamates derived from arylalkylamines. - Google Patents

Carbamates derived from arylalkylamines. Download PDF

Info

Publication number: OA12300A
Authority: OA; OAPI
Prior art keywords: several; daims; alkoxyl; substituted; compound
Prior art date: 2000-06-27

Application number

OA1200200393A

Other languages

English (en)

Inventor

Charles Farrerons Gallemi

Juan Lorenzo Catena Ruiz

Anna Fernandez Serrat

Ignacio Jose Miquel Bono

Dolors Balsa Lopez

Jose Ignacio Bonilla Navarro

Carmen Lagunas Arnal

Carolina Salcedo Roca

Andres Fernandez Garcia

Original Assignee

S A L V A T Lab Sa

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.)

2000-06-27

Filing date

2001-06-25

Publication date

2006-05-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8494130&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA12300(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-06-25 Application filed by S A L V A T Lab Sa filed Critical S A L V A T Lab Sa

2006-05-12 Publication of OA12300A publication Critical patent/OA12300A/en

Links

150000004657 carbamic acid derivatives Chemical class 0.000 title abstract description 7
150000003975 aryl alkyl amines Chemical class 0.000 title description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 11
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims abstract description 6
206010046543 Urinary incontinence Diseases 0.000 claims abstract description 5
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 4
206010014561 Emphysema Diseases 0.000 claims abstract description 4
208000006673 asthma Diseases 0.000 claims abstract description 4
206010006451 bronchitis Diseases 0.000 claims abstract description 4
201000010099 disease Diseases 0.000 claims abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
206010039083 rhinitis Diseases 0.000 claims abstract description 4
150000001204 N-oxides Chemical class 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 28
-1 cyclopropyl,cyclobutyl Chemical group 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
208000023504 respiratory system disease Diseases 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
102000017926 CHRM2 Human genes 0.000 abstract description 7
101150012960 Chrm2 gene Proteins 0.000 abstract description 7
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 abstract description 5
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 abstract description 5
239000005557 antagonist Substances 0.000 abstract description 5
206010006458 Bronchitis chronic Diseases 0.000 abstract description 3
208000007451 chronic bronchitis Diseases 0.000 abstract description 3
206010020853 Hypertonic bladder Diseases 0.000 abstract description 2
150000001412 amines Chemical class 0.000 abstract description 2
210000002345 respiratory system Anatomy 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
150000003254 radicals Chemical group 0.000 abstract 1
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
239000002904 solvent Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
102000017925 CHRM3 Human genes 0.000 description 7
101150060249 CHRM3 gene Proteins 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
229940126083 M3 antagonist Drugs 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229960002677 darifenacin Drugs 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229940044551 receptor antagonist Drugs 0.000 description 3
239000002464 receptor antagonist Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 description 2
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000012528 membrane Substances 0.000 description 2
230000003551 muscarinic effect Effects 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
229960004045 tolterodine Drugs 0.000 description 2
BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 2
IVLICPVPXWEGCA-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC2[C@@H](O)CN1CC2 IVLICPVPXWEGCA-ZETCQYMHSA-N 0.000 description 1
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
WGNZRZSJIVMRBU-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl carbonochloridate Chemical compound C1CC2C(OC(=O)Cl)CN1CC2 WGNZRZSJIVMRBU-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
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 1
229930003347 Atropine Natural products 0.000 description 1
102000017927 CHRM1 Human genes 0.000 description 1
102000017924 CHRM4 Human genes 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
101150073075 Chrm1 gene Proteins 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 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
102000007205 Muscarinic M2 Receptor Human genes 0.000 description 1
108010008407 Muscarinic M2 Receptor Proteins 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
208000006550 Mydriasis Diseases 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
101100107916 Xenopus laevis chrm4 gene Proteins 0.000 description 1
DOAKXPDAEYUFEQ-FJXQXJEOSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] carbonochloridate;hydrochloride Chemical compound Cl.C1CC2[C@@H](OC(=O)Cl)CN1CC2 DOAKXPDAEYUFEQ-FJXQXJEOSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
238000003556 assay Methods 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
230000007883 bronchodilation Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
206010013781 dry mouth Diseases 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
230000005176 gastrointestinal motility Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000007429 general method Methods 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
230000000762 glandular Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960005434 oxybutynin Drugs 0.000 description 1
230000001734 parasympathetic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
210000003079 salivary gland Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B27/00—Photographic printing apparatus
- G03B27/02—Exposure apparatus for contact printing
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B27/00—Photographic printing apparatus
- G03B27/02—Exposure apparatus for contact printing
- G03B27/14—Details
- G03B27/16—Illumination arrangements, e.g. positioning of lamps, positioning of reflectors
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B27/00—Photographic printing apparatus
- G03B27/02—Exposure apparatus for contact printing
- G03B27/14—Details
- G03B27/30—Details adapted to be combined with processing apparatus
- G03B27/303—Gas processing
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03D—APPARATUS FOR PROCESSING EXPOSED PHOTOGRAPHIC MATERIALS; ACCESSORIES THEREFOR
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OA1200200393A 2000-06-27 2001-06-25 Carbamates derived from arylalkylamines. OA12300A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES200001661		2000-06-27

Publications (1)

Publication Number	Publication Date
OA12300A true OA12300A (en)	2006-05-12

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ID=8494130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200393A OA12300A (en)	2000-06-27	2001-06-25	Carbamates derived from arylalkylamines.

Country Status (29)

Country	Link
US (2)	US6916828B2 (fr)
EP (1)	EP1300407B2 (fr)
JP (1)	JP5046465B2 (fr)
KR (1)	KR100751981B1 (fr)
CN (1)	CN1227251C (fr)
AP (1)	AP1420A (fr)
AT (1)	ATE260277T1 (fr)
AU (2)	AU2001266100B9 (fr)
BG (1)	BG66102B1 (fr)
BR (1)	BR0112297A (fr)
CA (1)	CA2414514C (fr)
CR (1)	CR6889A (fr)
CZ (1)	CZ294251B6 (fr)
DE (2)	DE20122417U1 (fr)
DK (1)	DK1300407T4 (fr)
EA (1)	EA005520B1 (fr)
ES (1)	ES2213703T5 (fr)
HU (1)	HU229306B1 (fr)
IL (1)	IL153707A0 (fr)
MX (1)	MXPA03000141A (fr)
NO (1)	NO328499B1 (fr)
OA (1)	OA12300A (fr)
PL (1)	PL201530B1 (fr)
PT (1)	PT1300407E (fr)
SI (1)	SI1300407T2 (fr)
TR (1)	TR200400420T4 (fr)
UA (1)	UA72632C2 (fr)
WO (1)	WO2002000652A1 (fr)
ZA (1)	ZA200300644B (fr)

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2001
- 2001-06-25 AU AU2001266100A patent/AU2001266100B9/en not_active Ceased
- 2001-06-25 IL IL15370701A patent/IL153707A0/xx not_active IP Right Cessation
- 2001-06-25 OA OA1200200393A patent/OA12300A/en unknown
- 2001-06-25 ES ES01943553T patent/ES2213703T5/es not_active Expired - Lifetime
- 2001-06-25 DE DE20122417U patent/DE20122417U1/de not_active Expired - Lifetime
- 2001-06-25 MX MXPA03000141A patent/MXPA03000141A/es active IP Right Grant
- 2001-06-25 HU HU0301414A patent/HU229306B1/hu not_active IP Right Cessation
- 2001-06-25 BR BR0112297-5A patent/BR0112297A/pt active Search and Examination
- 2001-06-25 AU AU6610001A patent/AU6610001A/xx not_active Withdrawn
- 2001-06-25 PL PL359333A patent/PL201530B1/pl unknown
- 2001-06-25 DK DK01943553.6T patent/DK1300407T4/da active
- 2001-06-25 PT PT01943553T patent/PT1300407E/pt unknown
- 2001-06-25 AP APAP/P/2003/002722A patent/AP1420A/en active
- 2001-06-25 TR TR2004/00420T patent/TR200400420T4/xx unknown
- 2001-06-25 EP EP01943553A patent/EP1300407B2/fr not_active Expired - Lifetime
- 2001-06-25 EA EA200300072A patent/EA005520B1/ru not_active IP Right Cessation
- 2001-06-25 CZ CZ2003261A patent/CZ294251B6/cs not_active IP Right Cessation
- 2001-06-25 KR KR1020027017706A patent/KR100751981B1/ko not_active Expired - Fee Related
- 2001-06-25 CA CA002414514A patent/CA2414514C/fr not_active Expired - Fee Related
- 2001-06-25 US US10/312,227 patent/US6916828B2/en not_active Expired - Fee Related
- 2001-06-25 UA UA2003010718A patent/UA72632C2/uk unknown
- 2001-06-25 WO PCT/ES2001/000252 patent/WO2002000652A1/fr not_active Ceased
- 2001-06-25 DE DE60102160T patent/DE60102160T3/de not_active Expired - Lifetime
- 2001-06-25 AT AT01943553T patent/ATE260277T1/de active
- 2001-06-25 CN CNB018148042A patent/CN1227251C/zh not_active Expired - Fee Related
- 2001-06-25 JP JP2002505776A patent/JP5046465B2/ja not_active Expired - Fee Related
- 2001-06-25 SI SI200130075T patent/SI1300407T2/sl unknown
2002
- 2002-12-23 NO NO20026211A patent/NO328499B1/no not_active IP Right Cessation
2003
- 2003-01-17 BG BG107474A patent/BG66102B1/bg unknown
- 2003-01-20 CR CR6889A patent/CR6889A/es not_active Application Discontinuation
- 2003-01-23 ZA ZA200300644A patent/ZA200300644B/en unknown
2004
- 2004-06-23 US US10/875,592 patent/US7115629B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MXPA03000141A (es)	2003-05-27
DE60102160T2 (de)	2004-09-09
CZ2003261A3 (cs)	2003-06-18
AU6610001A (en)	2002-01-08
IL153707A0 (en)	2003-07-06
SI1300407T1 (en)	2004-06-30
CR6889A (es)	2008-08-21
EP1300407A1 (fr)	2003-04-09
US20040063950A1 (en)	2004-04-01
CZ294251B6 (cs)	2004-11-10
NO328499B1 (no)	2010-03-01
JP5046465B2 (ja)	2012-10-10
EA200300072A1 (ru)	2003-06-26
AU2001266100B2 (en)	2005-06-30
HUP0301414A3 (en)	2008-03-28
KR20030022159A (ko)	2003-03-15
AP2003002722A0 (en)	2003-06-30
HK1054934A1 (en)	2003-12-19
US7115629B2 (en)	2006-10-03
ES2213703T3 (es)	2004-09-01
CA2414514A1 (fr)	2002-01-03
KR100751981B1 (ko)	2007-08-28
US20040235887A1 (en)	2004-11-25
PT1300407E (pt)	2004-05-31
US6916828B2 (en)	2005-07-12
EP1300407B1 (fr)	2004-02-25
HU229306B1 (en)	2013-10-28
ES2213703T5 (es)	2011-11-02
BG107474A (en)	2003-09-30
DE60102160D1 (de)	2004-04-01
EA005520B1 (ru)	2005-04-28
AP1420A (en)	2005-05-30
PL201530B1 (pl)	2009-04-30
NO20026211D0 (no)	2002-12-23
TR200400420T4 (tr)	2004-03-22
JP2004501916A (ja)	2004-01-22
ATE260277T1 (de)	2004-03-15
EP1300407B2 (fr)	2011-06-08
NO20026211L (no)	2003-02-26
DE20122417U1 (de)	2005-08-04
UA72632C2 (uk)	2005-03-15
ZA200300644B (en)	2004-02-10
BG66102B1 (bg)	2011-04-29
SI1300407T2 (sl)	2011-09-30
PL359333A1 (en)	2004-08-23
DK1300407T3 (da)	2004-03-22
WO2002000652A1 (fr)	2002-01-03
AU2001266100B9 (en)	2005-10-06
DE60102160T3 (de)	2012-05-03
CN1449396A (zh)	2003-10-15
BR0112297A (pt)	2003-05-06
DK1300407T4 (da)	2011-09-05
HUP0301414A2 (hu)	2003-09-29
CA2414514C (fr)	2009-12-22
CN1227251C (zh)	2005-11-16

Publication	Publication Date	Title
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