NO318609B1 - Kinolin- og kinazolinforbindelser nyttige i terapi, spesielt i behandlingen av benign prostatisk hyperplasi - Google Patents
Kinolin- og kinazolinforbindelser nyttige i terapi, spesielt i behandlingen av benign prostatisk hyperplasi Download PDFInfo
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- NO318609B1 NO318609B1 NO19993396A NO993396A NO318609B1 NO 318609 B1 NO318609 B1 NO 318609B1 NO 19993396 A NO19993396 A NO 19993396A NO 993396 A NO993396 A NO 993396A NO 318609 B1 NO318609 B1 NO 318609B1
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- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title claims description 7
- 208000004403 Prostatic Hyperplasia Diseases 0.000 title claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 5
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 2
- 238000002560 therapeutic procedure Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 318
- -1 1,4-diazepan-1-yl Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
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- 238000001665 trituration Methods 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 239000000284 extract Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 7
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 7
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 239000012071 phase Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- WTFFOOAJSDVASL-UHFFFAOYSA-N tributyl(pyrimidin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CC=N1 WTFFOOAJSDVASL-UHFFFAOYSA-N 0.000 description 6
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- 125000000623 heterocyclic group Chemical group 0.000 description 5
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- 229960001802 phenylephrine Drugs 0.000 description 5
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- 238000009472 formulation Methods 0.000 description 4
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- WDPWEXWMQDRXAL-UHFFFAOYSA-N tert-butyl 1,4-diazepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCNCC1 WDPWEXWMQDRXAL-UHFFFAOYSA-N 0.000 description 1
- CWQHKGSNPFVPJN-UHFFFAOYSA-N tert-butyl 4-(1,2,3,4-tetrahydroisoquinolin-7-ylsulfonyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC=C(CCNC2)C2=C1 CWQHKGSNPFVPJN-UHFFFAOYSA-N 0.000 description 1
- RKEKDCDFCAEABK-UHFFFAOYSA-N tert-butyl 4-(morpholine-4-carbonyl)-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1C(=O)N1CCOCC1 RKEKDCDFCAEABK-UHFFFAOYSA-N 0.000 description 1
- RVDSVNBBJMUXOY-UHFFFAOYSA-N tert-butyl 4-[[2-(4-amino-6,7-dimethoxy-5-pyridin-2-ylquinazolin-2-yl)-3,4-dihydro-1h-isoquinolin-7-yl]sulfonyl]piperazine-1-carboxylate Chemical compound COC=1C(OC)=CC2=NC(N3CC4=CC(=CC=C4CC3)S(=O)(=O)N3CCN(CC3)C(=O)OC(C)(C)C)=NC(N)=C2C=1C1=CC=CC=N1 RVDSVNBBJMUXOY-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9700504.5A GB9700504D0 (en) | 1997-01-11 | 1997-01-11 | Pharmaceutical compounds |
| PCT/EP1998/000143 WO1998030560A1 (en) | 1997-01-11 | 1998-01-06 | Quinoline and quinazoline compounds useful in therapy, particularly in the treatment of begnin prostatic hyperplasia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993396D0 NO993396D0 (no) | 1999-07-09 |
| NO993396L NO993396L (no) | 1999-07-09 |
| NO318609B1 true NO318609B1 (no) | 2005-04-18 |
Family
ID=10805838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993396A NO318609B1 (no) | 1997-01-11 | 1999-07-09 | Kinolin- og kinazolinforbindelser nyttige i terapi, spesielt i behandlingen av benign prostatisk hyperplasi |
Country Status (45)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9700504D0 (en) | 1997-01-11 | 1997-02-26 | Pfizer Ltd | Pharmaceutical compounds |
| GB9708917D0 (en) * | 1997-05-01 | 1997-06-25 | Pfizer Ltd | Compounds useful in therapy |
| IL141235A (en) | 2000-02-09 | 2012-04-30 | Novartis Int Pharm Ltd | Combined use of an alpha-adrenoceptor antagonist and a muscarinic antagonist in the preparation of a drug for the treatment of non-malignant prostatic hyperplasia |
| JP3857919B2 (ja) | 2000-03-03 | 2006-12-13 | ファイザー・インク | ４−アミノ−６，７−ジメトキシ−２−（５−メタンスルホンアミド−１，２，３，４−テトラヒドロイソキノル−２−イル）−５−（２−ピリジル）キナゾリンメシラートおよび多形 |
| BR0113585A (pt) | 2000-08-31 | 2003-07-29 | Hoffmann La Roche | Derivados quinazolina como antagonistas adrenérgicos alfa-1 |
| US6900220B2 (en) | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
| JP4031363B2 (ja) * | 2001-01-02 | 2008-01-09 | エフ．ホフマン−ラ ロシュ アーゲー | α−１Ａ／Ｂアドレナリン作動性受容体拮抗薬としてのキナゾロン誘導体 |
| US6734303B2 (en) | 2001-05-18 | 2004-05-11 | Pfizer Inc. | Process for the production of quinazolines |
| GB0112061D0 (en) * | 2001-05-18 | 2001-07-11 | Pfizer Ltd | Process for the production of quinazolines |
| US7163696B2 (en) | 2001-10-11 | 2007-01-16 | Pfizer Inc. | Pharmaceutical formulations |
| GB0124455D0 (en) * | 2001-10-11 | 2001-12-05 | Pfizer Ltd | Pharmaceutical formulations |
| GB0206033D0 (en) * | 2002-03-14 | 2002-04-24 | Pfizer Ltd | Compounds useful in therapy |
| EP2280003B1 (en) | 2002-07-15 | 2014-04-02 | Symphony Evolution, Inc. | Process for preparing receptor-type kinase modulators |
| GB0219961D0 (en) | 2002-08-28 | 2002-10-02 | Pfizer Ltd | Oxytocin inhibitors |
| GB0221579D0 (en) * | 2002-09-17 | 2002-10-23 | Pfizer Ltd | Combinations of atorvastatin and, adrenergic receptor antagonists |
| GB0221582D0 (en) * | 2002-09-17 | 2002-10-23 | Pfizer Ltd | Method of treatment |
| ATE386741T1 (de) | 2002-09-26 | 2008-03-15 | Pfizer | Pyrazolamide zur behandlung von hiv-infektionen |
| GB0225908D0 (en) * | 2002-11-06 | 2002-12-11 | Pfizer Ltd | Treatment of female sexual dysfunction |
| WO2004054560A1 (en) | 2002-12-13 | 2004-07-01 | Warner-Lambert Company Llc | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| MXPA06000185A (es) * | 2003-07-02 | 2006-04-11 | Hoffmann La Roche | Derivados de quinazolinas 5-sustituidas. |
| US7291640B2 (en) | 2003-09-22 | 2007-11-06 | Pfizer Inc. | Substituted triazole derivatives as oxytocin antagonists |
| SI2210607T1 (sl) | 2003-09-26 | 2011-11-30 | Exelixis Inc | N- 3-fluoro-4- 6- metiloksi)-7- 3-morfolin-4-ilpropil)oksi)kinolin-4 -il)oksi)fenil)-N'- 4-flurofenil)ciklopropan-1 1-dikarboksamid za zdravljenje raka |
| WO2005089804A2 (en) * | 2004-03-16 | 2005-09-29 | Pfizer Limited | Combinations of hmg-coa reductase inhibitors and alpha1 adrenergic receptor antagonists |
| KR20050092519A (ko) * | 2004-03-16 | 2005-09-22 | 화이자 인코포레이티드 | 아토르바스타틴 및 α1-아드레날린성 수용체 길항제의 조합 |
| GEP20084550B (en) | 2004-04-30 | 2008-11-25 | Warner Lambert Co | Substituted morpholine compounds for the treatment of central nervous system disorders |
| WO2008084493A2 (en) * | 2007-01-09 | 2008-07-17 | Unichem Laboratories Limited | A novel process for the preparation of 2-halo-4-aminoquinazolines |
| JP2009126785A (ja) * | 2007-11-19 | 2009-06-11 | Mitsubishi Gas Chem Co Inc | ２−ヨード−３，４−ジメトキシベンゾニトリルの製造方法 |
| JP2009126784A (ja) * | 2007-11-19 | 2009-06-11 | Mitsubishi Gas Chem Co Inc | ２−ヨード−３，４−ジメトキシベンゾニトリルの製造方法。 |
| KR102088588B1 (ko) | 2009-01-16 | 2020-03-12 | 엑셀리시스, 인코포레이티드 | Ｎ-（４-｛〔６，７-비스（메틸옥시）퀴놀린-4-일〕옥시｝페닐）-ｎ＇-（４-플루오로페닐）사이클로프로판-1,1-디카르복사미드의 말산염 및 그 결정형 |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| NZ724691A (en) * | 2014-03-24 | 2018-02-23 | Guangdong Zhongsheng Pharmaceutical Co Ltd | Quinoline derivatives as smo inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US875506A (en) * | 1907-03-19 | 1907-12-31 | Berry H Collins | Guiding attachment for penholders. |
| GB1390015A (en) * | 1971-05-07 | 1975-04-09 | Koninklijke Pharma Fab Nv | 4-amino-quinazoline compounds |
| US4026894A (en) * | 1975-10-14 | 1977-05-31 | Abbott Laboratories | Antihypertensive agents |
| US4098788A (en) * | 1977-06-20 | 1978-07-04 | Bristol-Myers Company | Process for preparing quinazolines |
| GR79603B (cs) | 1982-07-24 | 1984-10-31 | Pfizer | |
| GB8506174D0 (en) * | 1985-03-09 | 1985-04-11 | Pfizer Ltd | 4-amino-6 7-dimethoxy-2-piperazin-1-ylquinazoline derivatives |
| IT1270993B (it) | 1994-03-18 | 1997-05-26 | Recordati Chem Pharm | Derivati chinzolilamminici attivi come alfa-antagonisti |
| NZ325248A (en) | 1995-12-23 | 1999-09-29 | Pfizer Res & Dev | Quinoline and quinazoline compounds useful in therapy |
| GB9700504D0 (en) | 1997-01-11 | 1997-02-26 | Pfizer Ltd | Pharmaceutical compounds |
| GB9708917D0 (en) * | 1997-05-01 | 1997-06-25 | Pfizer Ltd | Compounds useful in therapy |
| GB9711650D0 (en) | 1997-06-05 | 1997-07-30 | Pfizer Ltd | Compounds useful in therapy |
-
1997
- 1997-01-11 GB GBGB9700504.5A patent/GB9700504D0/en active Pending
- 1997-11-18 TW TW086117203A patent/TW444013B/zh not_active IP Right Cessation
- 1997-12-13 SA SA97180705A patent/SA97180705B1/ar unknown
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1998
- 1998-01-05 HN HN1998000002A patent/HN1998000002A/es unknown
- 1998-01-05 PE PE1998000006A patent/PE44499A1/es not_active Application Discontinuation
- 1998-01-06 KR KR1019997006241A patent/KR100347472B1/ko not_active IP Right Cessation
- 1998-01-06 HU HU0000942A patent/HUP0000942A3/hu unknown
- 1998-01-06 DK DK98904058T patent/DK0968208T3/da active
- 1998-01-06 DE DE69815313T patent/DE69815313T2/de not_active Expired - Lifetime
- 1998-01-06 IL IL13076298A patent/IL130762A/xx not_active IP Right Cessation
- 1998-01-06 BR BR9807068-1A patent/BR9807068A/pt not_active Application Discontinuation
- 1998-01-06 YU YU31699A patent/YU31699A/sh unknown
- 1998-01-06 EP EP98904058A patent/EP0968208B1/en not_active Expired - Lifetime
- 1998-01-06 CN CNB011432918A patent/CN1191249C/zh not_active Expired - Fee Related
- 1998-01-06 EA EA199900531A patent/EA002851B1/ru not_active IP Right Cessation
- 1998-01-06 AU AU62088/98A patent/AU724990B2/en not_active Ceased
- 1998-01-06 PL PL98334678A patent/PL334678A1/xx unknown
- 1998-01-06 PA PA19988444301A patent/PA8444301A1/es unknown
- 1998-01-06 NZ NZ336302A patent/NZ336302A/xx unknown
- 1998-01-06 AP APAP/P/1998/001175A patent/AP819A/en active
- 1998-01-06 WO PCT/EP1998/000143 patent/WO1998030560A1/en active IP Right Grant
- 1998-01-06 AT AT98904058T patent/ATE242238T1/de not_active IP Right Cessation
- 1998-01-06 SK SK907-99A patent/SK284779B6/sk unknown
- 1998-01-06 JP JP53056598A patent/JP3357677B2/ja not_active Expired - Lifetime
- 1998-01-06 SI SI9830477T patent/SI0968208T1/xx unknown
- 1998-01-06 CN CN98801748A patent/CN1093858C/zh not_active Expired - Fee Related
- 1998-01-06 CZ CZ19992436A patent/CZ295580B6/cs not_active IP Right Cessation
- 1998-01-06 CA CA002277473A patent/CA2277473C/en not_active Expired - Fee Related
- 1998-01-06 ES ES98904058T patent/ES2198695T3/es not_active Expired - Lifetime
- 1998-01-06 PT PT98904058T patent/PT968208E/pt unknown
- 1998-01-06 US US09/341,228 patent/US6169093B1/en not_active Expired - Lifetime
- 1998-01-06 TR TR1999/01604T patent/TR199901604T2/xx unknown
- 1998-01-06 ID IDW990660A patent/ID21863A/id unknown
- 1998-01-07 TN TNTNSN98004A patent/TNSN98004A1/fr unknown
- 1998-01-07 MA MA24920A patent/MA26465A1/fr unknown
- 1998-01-08 AR ARP980100091A patent/AR010396A1/es unknown
- 1998-01-08 HR HR980010A patent/HRP980010B1/xx not_active IP Right Cessation
- 1998-01-09 MY MYPI98000094A patent/MY119623A/en unknown
- 1998-01-09 ZA ZA98166A patent/ZA98166B/xx unknown
- 1998-06-01 UA UA99073901A patent/UA62945C2/uk unknown
- 1998-06-07 DZ DZ980004A patent/DZ2394A1/xx active
-
1999
- 1999-06-25 IS IS5093A patent/IS2012B/is unknown
- 1999-07-07 BG BG103560A patent/BG63918B1/bg unknown
- 1999-07-08 OA OA9900152A patent/OA11074A/en unknown
- 1999-07-09 NO NO19993396A patent/NO318609B1/no unknown
-
2000
- 2000-06-02 US US09/586,503 patent/US6365599B1/en not_active Expired - Fee Related
- 2000-07-24 HK HK00104585A patent/HK1025327A1/xx not_active IP Right Cessation
-
2001
- 2001-11-13 US US10/007,753 patent/US6521629B2/en not_active Expired - Fee Related
-
2002
- 2002-12-13 US US10/318,902 patent/US6653302B2/en not_active Expired - Fee Related
-
2003
- 2003-09-17 HK HK03106677.4A patent/HK1054389B/zh not_active IP Right Cessation
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