JP2002526527A5 - - Google Patents
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- JP2002526527A5 JP2002526527A5 JP2000574506A JP2000574506A JP2002526527A5 JP 2002526527 A5 JP2002526527 A5 JP 2002526527A5 JP 2000574506 A JP2000574506 A JP 2000574506A JP 2000574506 A JP2000574506 A JP 2000574506A JP 2002526527 A5 JP2002526527 A5 JP 2002526527A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- cyano
- hydrogen
- methoxy
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- -1 trifluoromethylthio, trifluoromethylsulfinyl Chemical group 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 14
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000005236 alkanoylamino group Chemical group 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- KTMKRRPZPWUYKK-UHFFFAOYSA-N methylboronic acid Chemical compound CB(O)O KTMKRRPZPWUYKK-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000006268 reductive amination reaction Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- BCZHDPXODCPRIG-UHFFFAOYSA-N ethyl 3-cyano-4-methoxy-2-(trifluoromethylsulfonyloxy)naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(OS(=O)(=O)C(F)(F)F)C(C#N)=C(OC)C2=C1 BCZHDPXODCPRIG-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005281 alkyl ureido group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- IQOARHKBPKNTIZ-UHFFFAOYSA-N ethyl 3-bromo-2,4-dimethoxynaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(OC)C(Br)=C(OC)C2=C1 IQOARHKBPKNTIZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- KLOOCASJAUXYGD-UHFFFAOYSA-N methyl 2-methoxy-3-methylnaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(OC)C(C)=CC2=C1 KLOOCASJAUXYGD-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical class C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- NFKMPKOGCRBAJF-UHFFFAOYSA-N $l^{1}-azanylformonitrile Chemical compound [N]C#N NFKMPKOGCRBAJF-UHFFFAOYSA-N 0.000 description 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- SXUWNSGNETWEPM-UHFFFAOYSA-N 1-bromo-2-methoxy-3-methylnaphthalene Chemical compound C1=CC=CC2=C(Br)C(OC)=C(C)C=C21 SXUWNSGNETWEPM-UHFFFAOYSA-N 0.000 description 1
- JJLZGEMFDKIJJK-UHFFFAOYSA-N 2-(2-piperidin-4-ylphenyl)-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1C1CCNCC1 JJLZGEMFDKIJJK-UHFFFAOYSA-N 0.000 description 1
- OSJSCVZFFGVJBC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)pent-4-enal Chemical compound ClC1=CC=C(C(CC=C)C=O)C=C1Cl OSJSCVZFFGVJBC-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NPKPUCNATSURJQ-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]benzoic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC=C1C(O)=O NPKPUCNATSURJQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- VNCHKHUMIBLUHN-UHFFFAOYSA-N 2-methoxy-3-methylnaphthalene Chemical compound C1=CC=C2C=C(C)C(OC)=CC2=C1 VNCHKHUMIBLUHN-UHFFFAOYSA-N 0.000 description 1
- BOJLYRCLBOHHGY-UHFFFAOYSA-N 2-methoxy-3-methylnaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(OC)=C(C)C=C21 BOJLYRCLBOHHGY-UHFFFAOYSA-N 0.000 description 1
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 1
- PBQHREBFIVMQQQ-UHFFFAOYSA-N 3-(cyanomethyl)-2-methoxynaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(OC)=C(CC#N)C=C21 PBQHREBFIVMQQQ-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- ZZPKNEORLCOOLJ-UHFFFAOYSA-N 3-cyano-2-(2-methylpropyl)naphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(CC(C)C)=C(C#N)C=C21 ZZPKNEORLCOOLJ-UHFFFAOYSA-N 0.000 description 1
- ATXQEYJYKPSMRR-UHFFFAOYSA-N 3-cyano-2-prop-1-enylnaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C=CC)=C(C#N)C=C21 ATXQEYJYKPSMRR-UHFFFAOYSA-N 0.000 description 1
- YHWVUGRSUBTODN-UHFFFAOYSA-N 3-cyano-2-propan-2-yloxynaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(OC(C)C)=C(C#N)C=C21 YHWVUGRSUBTODN-UHFFFAOYSA-N 0.000 description 1
- ZLCRNEUNSMORST-UHFFFAOYSA-N 3-cyano-4-methoxy-2-methylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(OC)=C(C#N)C(C)=C(C(O)=O)C2=C1 ZLCRNEUNSMORST-UHFFFAOYSA-N 0.000 description 1
- SJTNTIRIRIPZDV-UHFFFAOYSA-N 3-methoxynaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(OC)=CC2=C1 SJTNTIRIRIPZDV-UHFFFAOYSA-N 0.000 description 1
- DBZMRRDZLZIAKF-UHFFFAOYSA-N 4-(4-bromo-2-methylsulfinylphenyl)piperidine Chemical compound CS(=O)C1=CC(Br)=CC=C1C1CCNCC1 DBZMRRDZLZIAKF-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- LKJUJDKVKOPUEE-UHFFFAOYSA-N benzo[f][1,3]benzodioxole-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(OCO3)C3=CC2=C1 LKJUJDKVKOPUEE-UHFFFAOYSA-N 0.000 description 1
- AIBSROMZPBPHAU-UHFFFAOYSA-N benzyl 4-(2-diethoxyphosphorylphenyl)piperidine-1-carboxylate Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1C1CCN(C(=O)OCC=2C=CC=CC=2)CC1 AIBSROMZPBPHAU-UHFFFAOYSA-N 0.000 description 1
- UPZJNTDFPXCTJQ-UHFFFAOYSA-N benzyl 4-[2-(trifluoromethylsulfonyloxy)phenyl]piperidine-1-carboxylate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1C1CCN(C(=O)OCC=2C=CC=CC=2)CC1 UPZJNTDFPXCTJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- KBLCCGJPHGETNR-UHFFFAOYSA-N methyl 3-cyano-2-(2-methylpropyl)naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(CC(C)C)C(C#N)=CC2=C1 KBLCCGJPHGETNR-UHFFFAOYSA-N 0.000 description 1
- GDDQFLRVLQWRHV-UHFFFAOYSA-N methyl 3-cyano-2-hydroxynaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(O)C(C#N)=CC2=C1 GDDQFLRVLQWRHV-UHFFFAOYSA-N 0.000 description 1
- OEMKLADDUDJLDY-UHFFFAOYSA-N methyl 3-cyano-2-prop-1-enylnaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(C=CC)C(C#N)=CC2=C1 OEMKLADDUDJLDY-UHFFFAOYSA-N 0.000 description 1
- MCYXSCDRXHNTBX-UHFFFAOYSA-N methyl 3-cyano-2-propan-2-yloxynaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(OC(C)C)C(C#N)=CC2=C1 MCYXSCDRXHNTBX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- CBMCZKMIOZYAHS-UHFFFAOYSA-N prop-1-enylboronic acid Chemical compound CC=CB(O)O CBMCZKMIOZYAHS-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 229940124530 sulfonamide Drugs 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9821699.7 | 1998-10-07 | ||
| GBGB9821699.7A GB9821699D0 (en) | 1998-10-07 | 1998-10-07 | Compounds |
| GBGB9906278.8A GB9906278D0 (en) | 1999-03-17 | 1999-03-17 | Compounds |
| GBGB9909839.4A GB9909839D0 (en) | 1999-04-30 | 1999-04-30 | Compounds |
| GB9906278.8 | 1999-04-30 | ||
| GB9909839.4 | 1999-04-30 | ||
| PCT/GB1999/003274 WO2000020389A1 (en) | 1998-10-07 | 1999-10-04 | Naphthalenecarboxamides as tachykinin receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002526527A JP2002526527A (ja) | 2002-08-20 |
| JP2002526527A5 true JP2002526527A5 (enExample) | 2006-11-24 |
Family
ID=27269502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000574506A Pending JP2002526527A (ja) | 1998-10-07 | 1999-10-04 | タキキニン受容体拮抗剤としてのナフタレンカルボキシアミド |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP1119551B1 (enExample) |
| JP (1) | JP2002526527A (enExample) |
| KR (1) | KR20010099675A (enExample) |
| CN (1) | CN1322196A (enExample) |
| AR (1) | AR024217A1 (enExample) |
| AT (1) | ATE286022T1 (enExample) |
| AU (1) | AU767002B2 (enExample) |
| BR (1) | BR9915904A (enExample) |
| CA (1) | CA2345133A1 (enExample) |
| DE (1) | DE69922979T2 (enExample) |
| GB (1) | GB9922521D0 (enExample) |
| HK (1) | HK1038919A1 (enExample) |
| IL (1) | IL142045A0 (enExample) |
| NO (1) | NO20011765L (enExample) |
| NZ (1) | NZ510582A (enExample) |
| WO (1) | WO2000020389A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6846814B2 (en) | 2000-04-06 | 2005-01-25 | Astra Zeneca Ab | Neurokinin antagonists for use as medicaments |
| DE60134735D1 (de) * | 2000-04-06 | 2008-08-21 | Astrazeneca Ab | Neue neurokinin-antagonisten zum gebrauch als arzneimittel |
| WO2001077069A1 (en) * | 2000-04-06 | 2001-10-18 | Astrazeneca Ab | Naphthamide neurokinin antagonists for use as medicaments |
| US6903092B2 (en) | 2000-04-06 | 2005-06-07 | Peter Bernstein | Naphthamide neurokinin antagonists for use as medicaments |
| GB0019008D0 (en) * | 2000-08-04 | 2000-09-27 | Astrazeneca Ab | Therapeutic compounds |
| SE0003476D0 (sv) * | 2000-09-28 | 2000-09-28 | Astrazeneca Ab | Compounds |
| SE0004827D0 (sv) | 2000-12-22 | 2000-12-22 | Astrazeneca Ab | Therapeutic compounds |
| SE0201938D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New process |
| ATE416162T1 (de) * | 2002-08-29 | 2008-12-15 | Astrazeneca Ab | Naphthamidderivate und deren verwendung |
| TW200508221A (en) | 2003-06-13 | 2005-03-01 | Astrazeneca Ab | New azetidine compounds |
| AR057828A1 (es) | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
| US8106208B2 (en) | 2006-05-18 | 2012-01-31 | Albireo Ab | Benzamide compounds that act as NK receptor antagonists |
| EP2117538A1 (en) | 2007-01-24 | 2009-11-18 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-) |
| WO2010056938A1 (en) | 2008-11-14 | 2010-05-20 | Theravance, Inc. | Process for preparing 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compounds |
| KR101430838B1 (ko) * | 2009-09-11 | 2014-08-18 | 가부시키가이샤 리코 | 치환기 이탈 화합물, 유기 반도체 재료, 상기 재료를 포함하는 유기 반도체 막, 상기 막을 포함하는 유기 전자 디바이스, 막상체의 제조 방법, π-전자 공역계 화합물 및 π-전자 공역계 화합물의 제조 방법 |
| EP2740735A4 (en) * | 2011-08-05 | 2014-09-03 | Teijin Ltd | CONDENSED POLYCYCLIC AROMATIC COMPOUND, AROMATIC POLYMER, AND PROCESS FOR SYNTHESIZING AROMATIC COMPOUND |
| EP4136068B1 (en) * | 2020-04-16 | 2024-07-10 | Basf Se | A process for the preparation of 4-cyanobenzoyl chlorides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE903957A1 (en) * | 1989-11-06 | 1991-05-08 | Sanofi Sa | Aromatic amine compounds, their method of preparation and¹pharmaceutical compositions in which they are present |
| IL99320A (en) * | 1990-09-05 | 1995-07-31 | Sanofi Sa | Arylalkylamines, their preparation and pharmaceutical compositions containing them |
| FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2688219B1 (fr) * | 1992-03-03 | 1994-07-08 | Sanofi Elf | Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant. |
| GB9310713D0 (en) * | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Aryl substituted heterocycles |
-
1999
- 1999-09-24 GB GBGB9922521.1A patent/GB9922521D0/en not_active Ceased
- 1999-10-04 CA CA002345133A patent/CA2345133A1/en not_active Abandoned
- 1999-10-04 CN CN99811926A patent/CN1322196A/zh active Pending
- 1999-10-04 DE DE69922979T patent/DE69922979T2/de not_active Expired - Fee Related
- 1999-10-04 EP EP99947738A patent/EP1119551B1/en not_active Expired - Lifetime
- 1999-10-04 AU AU61111/99A patent/AU767002B2/en not_active Ceased
- 1999-10-04 EP EP04006920A patent/EP1433783A3/en not_active Withdrawn
- 1999-10-04 JP JP2000574506A patent/JP2002526527A/ja active Pending
- 1999-10-04 KR KR1020017004356A patent/KR20010099675A/ko not_active Withdrawn
- 1999-10-04 WO PCT/GB1999/003274 patent/WO2000020389A1/en not_active Ceased
- 1999-10-04 NZ NZ510582A patent/NZ510582A/en unknown
- 1999-10-04 BR BR9915904-0A patent/BR9915904A/pt not_active IP Right Cessation
- 1999-10-04 IL IL14204599A patent/IL142045A0/xx unknown
- 1999-10-04 HK HK02100435.1A patent/HK1038919A1/zh unknown
- 1999-10-04 AT AT99947738T patent/ATE286022T1/de not_active IP Right Cessation
- 1999-10-06 AR ARP990105059A patent/AR024217A1/es not_active Application Discontinuation
-
2001
- 2001-04-06 NO NO20011765A patent/NO20011765L/no not_active Application Discontinuation
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