JPH11501329A - ゴナドトロピン放出ホルモン拮抗剤 - Google Patents

ゴナドトロピン放出ホルモン拮抗剤

Info

Publication number: JPH11501329A
Authority: JP; Japan
Prior art keywords: alkyl; substituted; compound; aryl; formula
Prior art date: 1995-12-14
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

Application number

JP9522123A

Other languages

English (en)

Japanese (ja)

Inventor

ゴーレツト，マーク

チユー，リン

フイツシヤー，マイケル・エイチ

ジロトラ，ナリンダー・エヌ

リン，ピーター

ウオルシユ，トーマス・エフ

ワイブラツト，マシユー・ジエイ

アシユトン，ウオラス・テイ

Original Assignee

メルクエンドカンパニーインコーポレーテッド

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.)

1995-12-14

Filing date

1996-12-10

Publication date

1999-02-02

1996-02-16 Priority claimed from GBGB9603369.1A external-priority patent/GB9603369D0/en

1996-12-10 Application filed by メルクエンドカンパニーインコーポレーテッド filed Critical メルクエンドカンパニーインコーポレーテッド

1999-02-02 Publication of JPH11501329A publication Critical patent/JPH11501329A/ja

Status Pending legal-status Critical Current

Links

239000002474 gonadorelin antagonist Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 164
150000003839 salts Chemical class 0.000 claims abstract description 20
101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 claims abstract description 16
239000003163 gonadal steroid hormone Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 172
-1 C1-C6Alkoxy Chemical group 0.000 claims description 150
238000000034 method Methods 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 37
125000003118 aryl group Chemical group 0.000 claims description 33
125000003710 aryl alkyl group Chemical group 0.000 claims description 30
125000003107 substituted aryl group Chemical group 0.000 claims description 28
239000000122 growth hormone Substances 0.000 claims description 21
102000018997 Growth Hormone Human genes 0.000 claims description 17
108010051696 Growth Hormone Proteins 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 12
229940088597 hormone Drugs 0.000 claims description 10
239000005556 hormone Substances 0.000 claims description 10
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
201000010260 leiomyoma Diseases 0.000 claims description 8
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
208000024891 symptom Diseases 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
206010046798 Uterine leiomyoma Diseases 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
201000009273 Endometriosis Diseases 0.000 claims description 5
206010020112 Hirsutism Diseases 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000001419 dependent effect Effects 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 claims description 5
229940035638 gonadotropin-releasing hormone Drugs 0.000 claims description 5
208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
201000002859 sleep apnea Diseases 0.000 claims description 5
201000007954 uterine fibroid Diseases 0.000 claims description 5
208000003200 Adenoma Diseases 0.000 claims description 4
206010062767 Hypophysitis Diseases 0.000 claims description 4
210000000481 breast Anatomy 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
206010025135 lupus erythematosus Diseases 0.000 claims description 4
210000003635 pituitary gland Anatomy 0.000 claims description 4
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 4
210000002307 prostate Anatomy 0.000 claims description 4
208000019116 sleep disease Diseases 0.000 claims description 4
206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
208000020221 Short stature Diseases 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000003245 coal Substances 0.000 claims description 3
239000003433 contraceptive agent Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
201000011510 cancer Diseases 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
210000002149 gonad Anatomy 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
208000006155 precocious puberty Diseases 0.000 claims description 2
230000035935 pregnancy Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 3
206010056438 Growth hormone deficiency Diseases 0.000 claims 2
208000020685 sleep-wake disease Diseases 0.000 claims 2
PDYVETAQJGWEHX-UHFFFAOYSA-N 3-[2-(3,5-dimethylphenyl)-3-[2-(5-pyridin-4-ylpentylamino)ethyl]-1h-indol-5-yl]-1,1-dimethylurea Chemical compound C12=CC(NC(=O)N(C)C)=CC=C2NC(C=2C=C(C)C=C(C)C=2)=C1CCNCCCCCC1=CC=NC=C1 PDYVETAQJGWEHX-UHFFFAOYSA-N 0.000 claims 1
230000002254 contraceptive effect Effects 0.000 claims 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
206010020718 hyperplasia Diseases 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
230000003248 secreting effect Effects 0.000 claims 1
210000002460 smooth muscle Anatomy 0.000 claims 1
230000004936 stimulating effect Effects 0.000 claims 1
208000010579 uterine corpus leiomyoma Diseases 0.000 claims 1
NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 abstract description 11
239000005557 antagonist Substances 0.000 abstract description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 212
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 204
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
239000000243 solution Substances 0.000 description 133
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 61
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 61
238000006243 chemical reaction Methods 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
235000019439 ethyl acetate Nutrition 0.000 description 51
239000000741 silica gel Substances 0.000 description 49
229910002027 silica gel Inorganic materials 0.000 description 49
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
229910052757 nitrogen Inorganic materials 0.000 description 41
238000003756 stirring Methods 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
239000012074 organic phase Substances 0.000 description 33
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
239000002253 acid Substances 0.000 description 30
238000003818 flash chromatography Methods 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
229910052938 sodium sulfate Inorganic materials 0.000 description 28
235000011152 sodium sulphate Nutrition 0.000 description 28
239000007787 solid Substances 0.000 description 28
239000000047 product Substances 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
239000000460 chlorine Substances 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
239000012141 concentrate Substances 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
150000001412 amines Chemical class 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000012267 brine Substances 0.000 description 18
239000003960 organic solvent Substances 0.000 description 18
235000008504 concentrate Nutrition 0.000 description 17
229920006395 saturated elastomer Polymers 0.000 description 17
238000004809 thin layer chromatography Methods 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 16
238000000746 purification Methods 0.000 description 16
239000002904 solvent Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
238000001819 mass spectrum Methods 0.000 description 15
238000010992 reflux Methods 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
229940079593 drug Drugs 0.000 description 14
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
239000000843 powder Substances 0.000 description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000010410 layer Substances 0.000 description 11
239000000463 material Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
125000006309 butyl amino group Chemical group 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
HESJZXOBRLYTEX-UHFFFAOYSA-N 2-(2-bromo-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=C(Br)NC2=C1 HESJZXOBRLYTEX-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
238000010828 elution Methods 0.000 description 9
229940121381 gonadotrophin releasing hormone (gnrh) antagonists Drugs 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 9
229910000033 sodium borohydride Inorganic materials 0.000 description 9
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000796 flavoring agent Substances 0.000 description 8
239000002609 medium Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000012746 preparative thin layer chromatography Methods 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
YHYICNMHQHRSAN-UHFFFAOYSA-N 2-[2-(1h-indol-3-yl)ethylamino]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1NCCC1=CNC2=CC=CC=C12 YHYICNMHQHRSAN-UHFFFAOYSA-N 0.000 description 7
108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
235000014113 dietary fatty acids Nutrition 0.000 description 7
239000000194 fatty acid Substances 0.000 description 7
229930195729 fatty acid Natural products 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
230000001817 pituitary effect Effects 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
238000002560 therapeutic procedure Methods 0.000 description 7
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 7
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
229940122361 Bisphosphonate Drugs 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
150000004663 bisphosphonates Chemical class 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
239000011575 calcium Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
235000013355 food flavoring agent Nutrition 0.000 description 6
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
229940050176 methyl chloride Drugs 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
238000003556 assay Methods 0.000 description 5
230000002950 deficient Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000006260 foam Substances 0.000 description 5
235000003599 food sweetener Nutrition 0.000 description 5
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000012046 mixed solvent Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000005192 partition Methods 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000375 suspending agent Substances 0.000 description 5
239000003765 sweetening agent Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
MKZHJJQCUIZEDE-UHFFFAOYSA-N 1-[(2-hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)COC=3C4=CC=CC=C4C=CC=3)C(C)C)=CC=CC2=C1 MKZHJJQCUIZEDE-UHFFFAOYSA-N 0.000 description 4
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QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
235000011082 potassium citrates Nutrition 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
229960000208 pralmorelin Drugs 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical group CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000021595 spermatogenesis Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
OWPIFQXNMLDXKW-UHFFFAOYSA-N tert-butyl indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 OWPIFQXNMLDXKW-UHFFFAOYSA-N 0.000 description 1
SZGHVYFJCAVREK-UHFFFAOYSA-N tert-butyl n-[2-[2-(3,5-dichlorophenyl)-5-(diethylcarbamoyl)-1h-indol-3-yl]ethyl]-n-(4-pyridin-3-ylbutyl)carbamate Chemical compound C12=CC(C(=O)N(CC)CC)=CC=C2NC(C=2C=C(Cl)C=C(Cl)C=2)=C1CCN(C(=O)OC(C)(C)C)CCCCC1=CC=CN=C1 SZGHVYFJCAVREK-UHFFFAOYSA-N 0.000 description 1
AOYDJZZSGSYJEI-UHFFFAOYSA-N tert-butyl n-[2-[2-(3,5-dimethylphenyl)-5-nitro-1h-indol-3-yl]ethyl]carbamate Chemical compound CC1=CC(C)=CC(C2=C(C3=CC(=CC=C3N2)[N+]([O-])=O)CCNC(=O)OC(C)(C)C)=C1 AOYDJZZSGSYJEI-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
LHPLBVKWTNRDGP-UHFFFAOYSA-N tert-butyl-dimethyl-[4-(3-methyl-1,2-oxazol-5-yl)butoxy]silane Chemical compound CC=1C=C(CCCCO[Si](C)(C)C(C)(C)C)ON=1 LHPLBVKWTNRDGP-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229960005324 tiludronic acid Drugs 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
238000003325 tomography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000006211 transdermal dosage form Substances 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
230000005740 tumor formation Effects 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
- 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
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
- 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)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Reproductive Health (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

JP9522123A 1995-12-14 1996-12-10 ゴナドトロピン放出ホルモン拮抗剤 Pending JPH11501329A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US863495P	1995-12-14	1995-12-14
GB9603369.1		1996-02-16
GBGB9603369.1A GB9603369D0 (en)	1996-02-16	1996-02-16	Antagonists of gonadotropin releasing hormone
GB60/008,634		1996-02-16
PCT/US1996/019443 WO1997021703A1 (en)	1995-12-14	1996-12-10	Antagonists of gonadotropin releasing hormone

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2000030819A Division JP2000186039A (ja)	1995-12-14	2000-02-08	ゴナドトロピン放出ホルモン拮抗剤を含む医薬組成物

Publications (1)

Publication Number	Publication Date
JPH11501329A true JPH11501329A (ja)	1999-02-02

Family

ID=26308742

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP9522123A Pending JPH11501329A (ja)	1995-12-14	1996-12-10	ゴナドトロピン放出ホルモン拮抗剤
JP2000030819A Pending JP2000186039A (ja)	1995-12-14	2000-02-08	ゴナドトロピン放出ホルモン拮抗剤を含む医薬組成物

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP2000030819A Pending JP2000186039A (ja)	1995-12-14	2000-02-08	ゴナドトロピン放出ホルモン拮抗剤を含む医薬組成物

Country Status (17)

Country	Link
EP (1)	EP0871624A1 (cs)
JP (2)	JPH11501329A (cs)
KR (1)	KR19990072124A (cs)
CN (1)	CN1208413A (cs)
AU (1)	AU709090B2 (cs)
CA (1)	CA2240048A1 (cs)
CZ (1)	CZ183298A3 (cs)
EA (1)	EA000829B1 (cs)
EE (1)	EE9800181A (cs)
HU (1)	HUP9902121A3 (cs)
IL (1)	IL124613A0 (cs)
MX (1)	MX9804850A (cs)
NO (1)	NO982731L (cs)
NZ (1)	NZ325014A (cs)
PL (1)	PL327132A1 (cs)
SK (1)	SK77598A3 (cs)
WO (1)	WO1997021703A1 (cs)

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GB9718833D0 (en)	1997-09-04	1997-11-12	Merck Sharp & Dohme	Therapeutic agents
JP2001520997A (ja) *	1997-10-28	2001-11-06	メルクエンドカムパニーインコーポレーテッド	性腺刺激ホルモン放出ホルモン拮抗薬
JP2002503661A (ja) *	1998-02-11	2002-02-05	メルクエンドカムパニーインコーポレーテッド	性腺刺激ホルモン放出ホルモン拮抗薬
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US5998432A (en) *	1998-04-02	1999-12-07	Merck & Co., Inc.	Antagonists of gonadotropin releasing hormone
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US5985892A (en) *	1998-04-02	1999-11-16	Merck & Co., Ltd.	Antagonists of gonadotropin releasing hormone
US6346534B1 (en)	1998-09-23	2002-02-12	Neurocrine Biosciences, Inc.	Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
EP1171125A1 (en)	1999-03-10	2002-01-16	Merck & Co., Inc.	6-azaindole compounds as antagonists of gonadotropin releasing hormone
CA2367121A1 (en)	1999-03-10	2000-09-14	Merck & Co., Inc.	6-azaindole compounds as antagonists of gonadotropin releasing hormone
AU3514200A (en)	1999-03-10	2000-09-28	Merck & Co., Inc.	6-azaindole compounds as antagonists of gonadotropin releasing hormone
EP1161431A4 (en) *	1999-03-10	2002-04-24	Merck & Co Inc	6-AZAINDOL COMPOUNDS AS AN ANTAGONISTS OF THE GONADOTROPIN RELEASE HORMONES
US6537998B1 (en)	1999-10-15	2003-03-25	Neurocrine Biosciences, Inc.	Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
WO2001055119A2 (en)	2000-01-25	2001-08-02	Neurocrine Biosciences, Inc.	Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
GB0022670D0 (en)	2000-09-15	2000-11-01	Astrazeneca Ab	Molecules
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1996
- 1996-12-10 SK SK775-98A patent/SK77598A3/sk unknown
- 1996-12-10 EP EP96943624A patent/EP0871624A1/en not_active Withdrawn
- 1996-12-10 CZ CZ981832A patent/CZ183298A3/cs unknown
- 1996-12-10 WO PCT/US1996/019443 patent/WO1997021703A1/en not_active Ceased
- 1996-12-10 EA EA199800564A patent/EA000829B1/ru not_active IP Right Cessation
- 1996-12-10 JP JP9522123A patent/JPH11501329A/ja active Pending
- 1996-12-10 AU AU12819/97A patent/AU709090B2/en not_active Ceased
- 1996-12-10 HU HU9902121A patent/HUP9902121A3/hu unknown
- 1996-12-10 EE EE9800181A patent/EE9800181A/xx unknown
- 1996-12-10 PL PL96327132A patent/PL327132A1/xx unknown
- 1996-12-10 IL IL12461396A patent/IL124613A0/xx unknown
- 1996-12-10 KR KR1019980704442A patent/KR19990072124A/ko not_active Withdrawn
- 1996-12-10 NZ NZ325014A patent/NZ325014A/en unknown
- 1996-12-10 CN CN96199901A patent/CN1208413A/zh active Pending
- 1996-12-10 CA CA002240048A patent/CA2240048A1/en not_active Abandoned
1998
- 1998-06-12 NO NO982731A patent/NO982731L/no not_active Application Discontinuation
- 1998-06-15 MX MX9804850A patent/MX9804850A/es unknown
2000
- 2000-02-08 JP JP2000030819A patent/JP2000186039A/ja active Pending

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Also Published As

Publication number	Publication date
IL124613A0 (en)	1998-12-06
JP2000186039A (ja)	2000-07-04
HUP9902121A2 (hu)	1999-10-28
EA000829B1 (ru)	2000-04-24
EA199800564A1 (ru)	1998-12-24
NZ325014A (en)	2000-06-23
AU709090B2 (en)	1999-08-19
CN1208413A (zh)	1999-02-17
KR19990072124A (ko)	1999-09-27
SK77598A3 (en)	1999-01-11
PL327132A1 (en)	1998-11-23
MX9804850A (es)	1998-09-30
HUP9902121A3 (en)	2001-05-28
NO982731D0 (no)	1998-06-12
EE9800181A (et)	1998-12-15
CA2240048A1 (en)	1997-06-19
WO1997021703A1 (en)	1997-06-19
EP0871624A1 (en)	1998-10-21
AU1281997A (en)	1997-07-03
NO982731L (no)	1998-08-13
CZ183298A3 (cs)	1998-09-16

Publication	Publication Date	Title
JPH11501329A (ja)	1999-02-02	ゴナドトロピン放出ホルモン拮抗剤
JP3230818B2 (ja)	2001-11-19	ゴナドトロピン放出ホルモン拮抗剤
US6197975B1 (en)	2001-03-06	Antagonists of gonadotropin releasing hormone
US5756507A (en)	1998-05-26	Antagonists of gonadotropin releasing hormone
JPH11504040A (ja)	1999-04-06	ゴナドトロピン放出ホルモン拮抗剤
JP2002502427A (ja)	2002-01-22	ゴナドトロピン放出ホルモンの拮抗薬
JP2002502426A (ja)	2002-01-22	ゴナドトロピン放出ホルモンの拮抗薬
JP2002502422A (ja)	2002-01-22	ゴナドトロピン放出ホルモンの拮抗薬
JP2002503252A (ja)	2002-01-29	ゴナドトロピン放出ホルモンの拮抗薬
JP2002520409A (ja)	2002-07-09	ゴナドトロピン放出ホルモン拮抗薬
JP2002510685A (ja)	2002-04-09	性腺刺激ホルモン放出ホルモン拮抗薬
JP2001520996A (ja)	2001-11-06	性腺刺激ホルモン放出ホルモン拮抗薬
JP2002510684A (ja)	2002-04-09	性腺刺激ホルモン放出ホルモン拮抗薬
JP2001520997A (ja)	2001-11-06	性腺刺激ホルモン放出ホルモン拮抗薬
US6159989A (en)	2000-12-12	Antagonists of gonadotropin releasing hormone
JP2002538205A (ja)	2002-11-12	性腺刺激ホルモン放出ホルモン拮抗薬としての６−アザインドール化合物
US6156767A (en)	2000-12-05	Antagonists of gonadotropin releasing hormone
JP2002503661A (ja)	2002-02-05	性腺刺激ホルモン放出ホルモン拮抗薬
JP2002538206A (ja)	2002-11-12	性腺刺激ホルモン放出ホルモン拮抗薬としての６−アザインドール化合物
JP2002502428A (ja)	2002-01-22	ゴナドトロピン放出ホルモンの拮抗薬
US6211224B1 (en)	2001-04-03	Antagonists of gonadotropin releasing hormone
US6159975A (en)	2000-12-12	Antagonists of gonadotropin releasing hormone

JPH11501329A - ゴナドトロピン放出ホルモン拮抗剤 - Google Patents

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