DE2310031C3 - 1 -Benzyl-1 H-indazol-3-carbonsäuren, -amide und -ester - Google Patents
1 -Benzyl-1 H-indazol-3-carbonsäuren, -amide und -esterInfo
- Publication number
- DE2310031C3 DE2310031C3 DE2310031A DE2310031A DE2310031C3 DE 2310031 C3 DE2310031 C3 DE 2310031C3 DE 2310031 A DE2310031 A DE 2310031A DE 2310031 A DE2310031 A DE 2310031A DE 2310031 C3 DE2310031 C3 DE 2310031C3
- Authority
- DE
- Germany
- Prior art keywords
- indazole
- chlorobenzyl
- carboxylic acid
- solution
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title description 7
- 150000002148 esters Chemical class 0.000 title description 6
- CDRCOZFGMPTGBL-UHFFFAOYSA-N 1-benzylindazole-3-carboxylic acid Chemical class C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=CC=C1 CDRCOZFGMPTGBL-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 230000000997 anti-spermatogenic effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- LZSHJNODQMYZMN-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]indazole-3-carbonitrile Chemical group C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C#N)=N1 LZSHJNODQMYZMN-UHFFFAOYSA-N 0.000 description 3
- -1 Ethyl 1-chlorobenzyl-1 H-indazole-3-carboxylate Chemical compound 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KVJTUQKSWFBPHG-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-indazolecarboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Cl)C=C1 KVJTUQKSWFBPHG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 210000001550 testis Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WACYDMHZSJDLTB-UHFFFAOYSA-N 1-[(2,4,5-trichlorophenyl)methyl]indazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC(Cl)=C(Cl)C=C1Cl WACYDMHZSJDLTB-UHFFFAOYSA-N 0.000 description 1
- DYMCJIUYDSLBSD-UHFFFAOYSA-N 1-[(2,4-dibromophenyl)methyl]indazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Br)C=C1Br DYMCJIUYDSLBSD-UHFFFAOYSA-N 0.000 description 1
- XAFMIJVTZLRIIA-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]indazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=CC=C1Cl XAFMIJVTZLRIIA-UHFFFAOYSA-N 0.000 description 1
- LHUBCIXMWFXTQH-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]indazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC1=CC=C(Br)C=C1 LHUBCIXMWFXTQH-UHFFFAOYSA-N 0.000 description 1
- JLPQNSLSENHOML-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]indazole-3-carbonyl chloride Chemical compound ClC1=CC=C(CN2N=C(C3=CC=CC=C23)C(=O)Cl)C=C1 JLPQNSLSENHOML-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- REHRQXVEAXFIML-UHFFFAOYSA-N 1h-indazole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=NNC2=C1 REHRQXVEAXFIML-UHFFFAOYSA-N 0.000 description 1
- BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-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
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010013710 Drug interaction Diseases 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
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940098194 antabuse Drugs 0.000 description 1
- 230000002221 antabuse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- CQBPOPVKDNHISM-UHFFFAOYSA-N propane-1,2,3-triol;propan-2-one Chemical compound CC(C)=O.OCC(O)CO CQBPOPVKDNHISM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48628/72A IT1052111B (it) | 1972-02-29 | 1972-02-29 | Acidi i benzil i h indazol 3 carbossilici sostituiti e loro derivati |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2310031A1 DE2310031A1 (de) | 1973-09-20 |
| DE2310031B2 DE2310031B2 (de) | 1979-11-15 |
| DE2310031C3 true DE2310031C3 (de) | 1980-07-31 |
Family
ID=11267725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2310031A Expired DE2310031C3 (de) | 1972-02-29 | 1973-02-28 | 1 -Benzyl-1 H-indazol-3-carbonsäuren, -amide und -ester |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3895026A (enExample) |
| CA (1) | CA994347A (enExample) |
| DE (1) | DE2310031C3 (enExample) |
| FR (1) | FR2181773B1 (enExample) |
| GB (1) | GB1381422A (enExample) |
| HU (1) | HU165172B (enExample) |
| IN (1) | IN139264B (enExample) |
| IT (1) | IT1052111B (enExample) |
| NL (1) | NL179729C (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1050741B (it) * | 1975-12-01 | 1981-03-20 | Acraf | Utilizzazione degli acidi i benzil ih indazol 3 carbossilici sostituiti e loro derivati nel campo della contraccezione femminile |
| US5229408A (en) * | 1988-07-15 | 1993-07-20 | Ici Pharma | 4-carbamoyl-1,2-dihydro-3H-indazol-3-one derivatives |
| US5914405A (en) * | 1997-10-07 | 1999-06-22 | Eli Lilly And Company | Process for preparing 3-substituted indazoles |
| US6001865A (en) * | 1999-05-04 | 1999-12-14 | Angelini Pharmaceuticals Inc. | 3-substituted 1-benzyl-1H-indazole derivatives as antifertility agents |
| KR100424341B1 (ko) * | 2001-10-23 | 2004-03-24 | 하나제약 주식회사 | 1-메틸인다졸-3-카르복실산의 제조방법 |
| CA2513575A1 (en) * | 2003-01-17 | 2004-08-05 | Threshold Pharmaceuticals, Inc. | Treatment of benign prostatic hyperplasia using energolytic agents |
| EP1599196A4 (en) * | 2003-01-17 | 2006-05-31 | Threshold Pharmaceuticals Inc | COMBINATION THERAPIES FOR CANCER TREATMENT |
| CN1956964B (zh) * | 2004-03-24 | 2011-06-15 | 詹森药业有限公司 | 四氢-吲唑大麻素调节剂 |
| WO2005120498A2 (en) * | 2004-06-03 | 2005-12-22 | Threshold Pharmaceuticals, Inc. | Method for synthesis of lonidamine and related indazole derivatives |
| WO2006010077A2 (en) * | 2004-07-08 | 2006-01-26 | Threshold Pharmaceuticals, Inc. | Prodrugs of lonidamine and lonidamine analogs |
| US7514463B2 (en) | 2004-08-20 | 2009-04-07 | University Of Kansas | Lonidamine analogues and their use in male contraception and cancer treatment |
| CN101759644B (zh) * | 2005-08-17 | 2011-11-02 | 杭州民生药业有限公司 | 氯尼达明的结晶形式iii、其制备方法和含有所述结晶形式iii的组合物 |
| CN101735151B (zh) * | 2005-08-17 | 2012-07-04 | 杭州民生药业有限公司 | 氯尼达明的结晶形式i、其制备方法和含有所述结晶形式i的组合物 |
| WO2011005759A2 (en) * | 2009-07-06 | 2011-01-13 | University Of Kansas | Lonidamine analogues for fertility management |
| JP6944442B2 (ja) | 2015-06-12 | 2021-10-06 | ベットーレ リミテッド ライアビリティー カンパニーＶｅｔｔｏｒｅ， Ｌｌｃ | 疾患を治療するためのｍｃｔ４阻害剤 |
| CN110114351B (zh) | 2016-12-12 | 2022-09-20 | 维托尔股份有限公司 | Mct4的杂环抑制剂 |
| CN116438162A (zh) * | 2020-09-17 | 2023-07-14 | 伊赛恩特制药公司 | Mas相关g蛋白受体x4的调节剂及相关产物和方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3007938A (en) * | 1959-04-17 | 1961-11-07 | Sterling Drug Inc | 1-(3-indazolecarbonyl)-hydrazines and their preparation |
| US3145215A (en) * | 1961-12-19 | 1964-08-18 | Sterling Drug Inc | Indazole derivatives |
| IL28032A (en) * | 1966-08-29 | 1971-08-25 | Acraf | Indazol-3-yl-oxyalkanoic acids and process for the preparation thereof |
| US3567721A (en) * | 1968-11-29 | 1971-03-02 | Geigy Chem Corp | Indazolecarboxylic acids and derivatives thereof |
| DE1948793A1 (de) * | 1969-09-26 | 1971-04-01 | Rhein Chemie Rheinau Gmbh | Verfahren zur Herstellung von 4,5,6,7-Tetrahydroindazolen |
-
1972
- 1972-02-29 IT IT48628/72A patent/IT1052111B/it active
-
1973
- 1973-02-09 US US330902A patent/US3895026A/en not_active Expired - Lifetime
- 1973-02-16 GB GB780673A patent/GB1381422A/en not_active Expired
- 1973-02-21 IN IN389/CAL/73A patent/IN139264B/en unknown
- 1973-02-22 CA CA164,360A patent/CA994347A/en not_active Expired
- 1973-02-26 NL NLAANVRAGE7302669,A patent/NL179729C/xx not_active IP Right Cessation
- 1973-02-27 HU HUAI224A patent/HU165172B/hu not_active IP Right Cessation
- 1973-02-28 FR FR7307055A patent/FR2181773B1/fr not_active Expired
- 1973-02-28 DE DE2310031A patent/DE2310031C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181773B1 (enExample) | 1975-12-26 |
| NL179729C (nl) | 1986-11-03 |
| NL179729B (nl) | 1986-06-02 |
| DE2310031B2 (de) | 1979-11-15 |
| IN139264B (enExample) | 1976-05-29 |
| FR2181773A1 (enExample) | 1973-12-07 |
| IT1052111B (it) | 1981-06-20 |
| US3895026A (en) | 1975-07-15 |
| NL7302669A (enExample) | 1973-08-31 |
| CA994347A (en) | 1976-08-03 |
| GB1381422A (en) | 1975-01-22 |
| HU165172B (enExample) | 1974-07-27 |
| DE2310031A1 (de) | 1973-09-20 |
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