NO330143B1 - Morfolinderivater, preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike for fremstilling av medikament for behandling av sykdom - Google Patents

Morfolinderivater, preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike for fremstilling av medikament for behandling av sykdom Download PDF

Info

Publication number: NO330143B1
Authority: NO; Norway
Prior art keywords: disorder; formula; compounds; depression; compound
Prior art date: 2002-12-10

Application number

NO20052557A

Other languages

English (en)

Norwegian (no)

Other versions

NO20052557L (no

NO20052557D0 (no

Inventor

Charlotte Moira Norfor Allerton

David Hepworth

Andrew Simon Cook

Stephen Kwok-Fung Wong

Andrew Douglas Baxter

Original Assignee

Pfizer

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.)

2002-12-10

Filing date

2005-05-26

Publication date

2011-02-21

2002-12-10 Priority claimed from GB0228787A external-priority patent/GB0228787D0/en

2003-04-11 Priority claimed from GB0308460A external-priority patent/GB0308460D0/en

2003-06-12 Priority claimed from GB0313606A external-priority patent/GB0313606D0/en

2005-05-26 Application filed by Pfizer filed Critical Pfizer

2005-05-26 Publication of NO20052557D0 publication Critical patent/NO20052557D0/no

2005-09-06 Publication of NO20052557L publication Critical patent/NO20052557L/no

2011-02-21 Publication of NO330143B1 publication Critical patent/NO330143B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 238
238000011282 treatment Methods 0.000 title claims abstract description 34
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 29
239000003814 drug Substances 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 21
238000004519 manufacturing process Methods 0.000 title description 6
201000010099 disease Diseases 0.000 title description 4
150000002780 morpholines Chemical class 0.000 title 1
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
229910052727 yttrium Inorganic materials 0.000 claims abstract description 9
201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 8
231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
239000012453 solvate Substances 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
208000035475 disorder Diseases 0.000 claims description 25
230000001568 sexual effect Effects 0.000 claims description 22
206010057671 Female sexual dysfunction Diseases 0.000 claims description 21
201000001881 impotence Diseases 0.000 claims description 20
208000021663 Female sexual arousal disease Diseases 0.000 claims description 16
208000010228 Erectile Dysfunction Diseases 0.000 claims description 15
229940079593 drug Drugs 0.000 claims description 13
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 11
208000020016 psychiatric disease Diseases 0.000 claims description 11
230000004770 neurodegeneration Effects 0.000 claims description 9
NHTSBJAUMOIPAS-ZOWNYOTGSA-N 3-[(2r)-4-propylmorpholin-2-yl]phenol;hydrochloride Chemical compound Cl.C1N(CCC)CCO[C@@H]1C1=CC=CC(O)=C1 NHTSBJAUMOIPAS-ZOWNYOTGSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
230000035946 sexual desire Effects 0.000 claims description 8
GGNXXNYKGWVORA-ZDUSSCGKSA-N 2-fluoro-5-[(2r)-4-propylmorpholin-2-yl]phenol Chemical compound C1N(CCC)CCO[C@@H]1C1=CC=C(F)C(O)=C1 GGNXXNYKGWVORA-ZDUSSCGKSA-N 0.000 claims description 7
206010011953 Decreased activity Diseases 0.000 claims description 7
208000002193 Pain Diseases 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
WYEGTIGJSHGEID-ZDUSSCGKSA-N pf-219,061 Chemical compound C1N(CCC)CCO[C@@H]1C1=CC=CC(O)=C1 WYEGTIGJSHGEID-ZDUSSCGKSA-N 0.000 claims description 7
206010012289 Dementia Diseases 0.000 claims description 6
206010012335 Dependence Diseases 0.000 claims description 6
208000018737 Parkinson disease Diseases 0.000 claims description 6
208000027520 Somatoform disease Diseases 0.000 claims description 6
230000007000 age related cognitive decline Effects 0.000 claims description 6
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
208000027753 pain disease Diseases 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
208000011580 syndromic disease Diseases 0.000 claims description 6
208000031424 hyperprolactinemia Diseases 0.000 claims description 5
208000024309 orgasm disease Diseases 0.000 claims description 5
DFTCYTDJDXZFSK-JQWIXIFHSA-N pf-592,379 Chemical compound O1C[C@H](C)N(CCC)C[C@H]1C1=CC=C(N)N=C1 DFTCYTDJDXZFSK-JQWIXIFHSA-N 0.000 claims description 5
210000005166 vasculature Anatomy 0.000 claims description 5
208000017701 Endocrine disease Diseases 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
208000027089 Parkinsonian disease Diseases 0.000 claims description 4
206010034010 Parkinsonism Diseases 0.000 claims description 4
201000009916 Postpartum depression Diseases 0.000 claims description 4
206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 4
206010047163 Vasospasm Diseases 0.000 claims description 4
230000002490 cerebral effect Effects 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
208000019899 phobic disease Diseases 0.000 claims description 4
206010036596 premature ejaculation Diseases 0.000 claims description 4
230000000306 recurrent effect Effects 0.000 claims description 4
208000022170 stress incontinence Diseases 0.000 claims description 4
208000024891 symptom Diseases 0.000 claims description 4
208000002271 trichotillomania Diseases 0.000 claims description 4
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
206010054196 Affect lability Diseases 0.000 claims description 3
208000008811 Agoraphobia Diseases 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010002650 Anorexia nervosa and bulimia Diseases 0.000 claims description 3
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
208000001573 Cataplexy Diseases 0.000 claims description 3
206010008025 Cerebellar ataxia Diseases 0.000 claims description 3
208000006561 Cluster Headache Diseases 0.000 claims description 3
206010011469 Crying Diseases 0.000 claims description 3
208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims description 3
208000030814 Eating disease Diseases 0.000 claims description 3
208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
208000001640 Fibromyalgia Diseases 0.000 claims description 3
206010019233 Headaches Diseases 0.000 claims description 3
GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
206010034912 Phobia Diseases 0.000 claims description 3
206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
206010043118 Tardive Dyskinesia Diseases 0.000 claims description 3
208000000323 Tourette Syndrome Diseases 0.000 claims description 3
208000016620 Tourette disease Diseases 0.000 claims description 3
208000022804 avoidant personality disease Diseases 0.000 claims description 3
229940049706 benzodiazepine Drugs 0.000 claims description 3
150000001557 benzodiazepines Chemical class 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
230000001684 chronic effect Effects 0.000 claims description 3
229960003920 cocaine Drugs 0.000 claims description 3
229960002069 diamorphine Drugs 0.000 claims description 3
235000014632 disordered eating Nutrition 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
231100000869 headache Toxicity 0.000 claims description 3
208000021267 infertility disease Diseases 0.000 claims description 3
206010023461 kleptomania Diseases 0.000 claims description 3
208000024714 major depressive disease Diseases 0.000 claims description 3
230000004899 motility Effects 0.000 claims description 3
239000003176 neuroleptic agent Substances 0.000 claims description 3
230000000701 neuroleptic effect Effects 0.000 claims description 3
229960002715 nicotine Drugs 0.000 claims description 3
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
208000019906 panic disease Diseases 0.000 claims description 3
230000001575 pathological effect Effects 0.000 claims description 3
208000022821 personality disease Diseases 0.000 claims description 3
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 3
229960002695 phenobarbital Drugs 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
230000028327 secretion Effects 0.000 claims description 3
230000035939 shock Effects 0.000 claims description 3
208000019116 sleep disease Diseases 0.000 claims description 3
208000020685 sleep-wake disease Diseases 0.000 claims description 3
201000001716 specific phobia Diseases 0.000 claims description 3
230000035882 stress Effects 0.000 claims description 3
208000019553 vascular disease Diseases 0.000 claims description 3
208000011688 Generalised anxiety disease Diseases 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
208000029364 generalized anxiety disease Diseases 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 2
229960001755 resorcinol Drugs 0.000 claims description 2
CHAXZAKOMAQMHM-VAZZWQITSA-N C[C@H]1CO[C@H](CN1CCC)C=1C=CC(=NC1)N.ClC1=C(C=C(C=C1)C1CN(CCO1)CCC)O.C(CC)N1CC(OCC1)C=1C=CC(=NC1)N Chemical compound C[C@H]1CO[C@H](CN1CCC)C=1C=CC(=NC1)N.ClC1=C(C=C(C=C1)C1CN(CCO1)CCC)O.C(CC)N1CC(OCC1)C=1C=CC(=NC1)N CHAXZAKOMAQMHM-VAZZWQITSA-N 0.000 claims 1
230000003109 amnesic effect Effects 0.000 claims 1
230000001314 paroxysmal effect Effects 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 6
229940052760 dopamine agonists Drugs 0.000 abstract description 2
239000003136 dopamine receptor stimulating agent Substances 0.000 abstract description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
229940002612 prodrug Drugs 0.000 abstract 1
239000000651 prodrug Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 208
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
210000004027 cell Anatomy 0.000 description 105
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 88
239000011541 reaction mixture Substances 0.000 description 84
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 83
238000005481 NMR spectroscopy Methods 0.000 description 76
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 52
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
238000000034 method Methods 0.000 description 45
239000003921 oil Substances 0.000 description 45
235000019198 oils Nutrition 0.000 description 45
229910001868 water Inorganic materials 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
238000007792 addition Methods 0.000 description 40
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 36
229960003089 pramipexole Drugs 0.000 description 36
FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 34
235000019439 ethyl acetate Nutrition 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
-1 lithium aluminum hydride Chemical compound 0.000 description 32
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 29
239000010410 layer Substances 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 28
239000002953 phosphate buffered saline Substances 0.000 description 28
238000010992 reflux Methods 0.000 description 28
239000000377 silicon dioxide Substances 0.000 description 26
239000007787 solid Substances 0.000 description 25
239000000556 agonist Substances 0.000 description 24
238000004440 column chromatography Methods 0.000 description 24
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
229910000041 hydrogen chloride Inorganic materials 0.000 description 24
238000012360 testing method Methods 0.000 description 24
239000012895 dilution Substances 0.000 description 23
239000012044 organic layer Substances 0.000 description 23
239000000047 product Substances 0.000 description 23
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
238000010790 dilution Methods 0.000 description 21
239000000284 extract Substances 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 18
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 18
238000004458 analytical method Methods 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
150000001408 amides Chemical class 0.000 description 15
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 14
150000001412 amines Chemical class 0.000 description 14
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 14
239000012230 colorless oil Substances 0.000 description 14
229960004132 diethyl ether Drugs 0.000 description 14
239000000463 material Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 13
238000003556 assay Methods 0.000 description 13
239000002590 phosphodiesterase V inhibitor Substances 0.000 description 13
238000000746 purification Methods 0.000 description 13
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
230000037007 arousal Effects 0.000 description 12
239000000872 buffer Substances 0.000 description 12
210000004392 genitalia Anatomy 0.000 description 12
230000004044 response Effects 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000012298 atmosphere Substances 0.000 description 11
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 10
239000012043 crude product Substances 0.000 description 10
238000010511 deprotection reaction Methods 0.000 description 10
230000001965 increasing effect Effects 0.000 description 10
VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 9
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
238000002474 experimental method Methods 0.000 description 9
239000003112 inhibitor Substances 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
230000000638 stimulation Effects 0.000 description 9
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 8
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
WAJNANMQOPCIPO-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidin-7-one Chemical class O=C1N=CN=C2C=NN=C12 WAJNANMQOPCIPO-UHFFFAOYSA-N 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
238000013207 serial dilution Methods 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
230000004913 activation Effects 0.000 description 7
150000001414 amino alcohols Chemical class 0.000 description 7
229910000085 borane Inorganic materials 0.000 description 7
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 7
239000000470 constituent Substances 0.000 description 7
ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 7
230000002265 prevention Effects 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
ODPCIOYTCBXSOI-UHFFFAOYSA-N 2-chloro-5-(4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CCOC1C1=CC=C(Cl)C(O)=C1 ODPCIOYTCBXSOI-UHFFFAOYSA-N 0.000 description 6
VZDVSSOINOOOOJ-ZDUSSCGKSA-N 5-[(2r)-4-propylmorpholin-2-yl]benzene-1,3-diol Chemical compound C1N(CCC)CCO[C@@H]1C1=CC(O)=CC(O)=C1 VZDVSSOINOOOOJ-ZDUSSCGKSA-N 0.000 description 6
229920000858 Cyclodextrin Polymers 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 6
239000006285 cell suspension Substances 0.000 description 6
150000002009 diols Chemical class 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000003306 harvesting Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
238000010606 normalization Methods 0.000 description 6
239000012071 phase Substances 0.000 description 6
210000002460 smooth muscle Anatomy 0.000 description 6
239000000725 suspension Substances 0.000 description 6
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
XDZBSCCFURVQOD-UHFFFAOYSA-N 2-bromo-4-(4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CCOC1C1=CC=C(O)C(Br)=C1 XDZBSCCFURVQOD-UHFFFAOYSA-N 0.000 description 5
DFTCYTDJDXZFSK-CMPLNLGQSA-N 5-[(2s,5s)-5-methyl-4-propylmorpholin-2-yl]pyridin-2-amine Chemical compound O1C[C@H](C)N(CCC)C[C@@H]1C1=CC=C(N)N=C1 DFTCYTDJDXZFSK-CMPLNLGQSA-N 0.000 description 5
208000019901 Anxiety disease Diseases 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 description 5
108090000525 Dopamine D3 Receptors Proteins 0.000 description 5
102000004073 Dopamine D3 Receptors Human genes 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
102000055135 Vasoactive Intestinal Peptide Human genes 0.000 description 5
108010003205 Vasoactive Intestinal Peptide Proteins 0.000 description 5
230000017531 blood circulation Effects 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000011575 calcium Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
229940011871 estrogen Drugs 0.000 description 5
239000000262 estrogen Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000005461 lubrication Methods 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
239000000843 powder Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
208000012201 sexual and gender identity disease Diseases 0.000 description 5
208000015891 sexual disease Diseases 0.000 description 5
BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000002560 therapeutic procedure Methods 0.000 description 5
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 4
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 4
HZWYVVALALXEJB-UHFFFAOYSA-N 2-amino-4-(4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CCOC1C1=CC=C(O)C(N)=C1 HZWYVVALALXEJB-UHFFFAOYSA-N 0.000 description 4
KOVNCVPOPFUEPN-UHFFFAOYSA-N 2-hydroxy-5-(4-propylmorpholin-2-yl)benzamide Chemical compound C1N(CCC)CCOC1C1=CC=C(O)C(C(N)=O)=C1 KOVNCVPOPFUEPN-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
101710095468 Cyclase Proteins 0.000 description 4
208000020401 Depressive disease Diseases 0.000 description 4
108090001111 Dopamine D2 Receptors Proteins 0.000 description 4
102000004980 Dopamine D2 Receptors Human genes 0.000 description 4
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 4
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
239000013543 active substance Substances 0.000 description 4
102000004305 alpha Adrenergic Receptors Human genes 0.000 description 4
108090000861 alpha Adrenergic Receptors Proteins 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
230000001430 anti-depressive effect Effects 0.000 description 4
229940005513 antidepressants Drugs 0.000 description 4
210000003169 central nervous system Anatomy 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000001514 detection method Methods 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
238000010494 dissociation reaction Methods 0.000 description 4
230000005593 dissociations Effects 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
238000002657 hormone replacement therapy Methods 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
208000014674 injury Diseases 0.000 description 4
239000008101 lactose Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 4
230000018052 penile erection Effects 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 4
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
229960003604 testosterone Drugs 0.000 description 4
238000010257 thawing Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
230000002792 vascular Effects 0.000 description 4
JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 3
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 3
KVQJVAOMYWTLEO-UHFFFAOYSA-N 2-chlorobutanoyl chloride Chemical compound CCC(Cl)C(Cl)=O KVQJVAOMYWTLEO-UHFFFAOYSA-N 0.000 description 3
WOLAYLBKITVXRB-ZSOXZCCMSA-N 3-[(5s)-5-methyl-4-propylmorpholin-2-yl]phenol Chemical compound O1C[C@H](C)N(CCC)CC1C1=CC=CC(O)=C1 WOLAYLBKITVXRB-ZSOXZCCMSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 3
MCVFILRDWPXYCN-UHFFFAOYSA-N 5-(4-propylmorpholin-2-yl)pyridin-2-amine Chemical compound C1N(CCC)CCOC1C1=CC=C(N)N=C1 MCVFILRDWPXYCN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
206010009094 Chronic paroxysmal hemicrania Diseases 0.000 description 3
101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 3
102000048186 Endothelin-converting enzyme 1 Human genes 0.000 description 3
108030001679 Endothelin-converting enzyme 1 Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
229930064664 L-arginine Natural products 0.000 description 3
235000014852 L-arginine Nutrition 0.000 description 3
206010024419 Libido decreased Diseases 0.000 description 3
206010057672 Male sexual dysfunction Diseases 0.000 description 3
102100024197 Membrane metallo-endopeptidase-like 1 Human genes 0.000 description 3
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 3
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 3
102000008299 Nitric Oxide Synthase Human genes 0.000 description 3
108010021487 Nitric Oxide Synthase Proteins 0.000 description 3
235000019502 Orange oil Nutrition 0.000 description 3
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 3
101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 3
ZIIQCSMRQKCOCT-YFKPBYRVSA-N S-nitroso-N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-YFKPBYRVSA-N 0.000 description 3
SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
102000030621 adenylate cyclase Human genes 0.000 description 3
108060000200 adenylate cyclase Proteins 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
210000003029 clitoris Anatomy 0.000 description 3
210000005226 corpus cavernosum Anatomy 0.000 description 3
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
229960002986 dinoprostone Drugs 0.000 description 3
238000003821 enantio-separation Methods 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000013100 final test Methods 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
208000017020 hypoactive sexual desire disease Diseases 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000002197 limbic effect Effects 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
239000002609 medium Substances 0.000 description 3
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000009245 menopause Effects 0.000 description 3
239000002858 neurotransmitter agent Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000010502 orange oil Substances 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 3
229960001723 oxytocin Drugs 0.000 description 3
208000007777 paroxysmal Hemicrania Diseases 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 3
230000001817 pituitary effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 3
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
229940075993 receptor modulator Drugs 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
230000001105 regulatory effect Effects 0.000 description 3
230000009329 sexual behaviour Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
WOXKDUGGOYFFRN-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 WOXKDUGGOYFFRN-IIBYNOLFSA-N 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
YKWCXUFYMYCVCS-RGMNGODLSA-N (2s)-2-(propylamino)propan-1-ol;hydrochloride Chemical compound Cl.CCCN[C@@H](C)CO YKWCXUFYMYCVCS-RGMNGODLSA-N 0.000 description 2
JDKLPDJLXHXHNV-MFVUMRCOSA-N (3s,6s,9r,12s,15s,23s)-15-[[(2s)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1h-imidazol-5-ylmethyl)-3-(1h-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxamide Chemical compound C([C@@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCNC(=O)C[C@@H](C(N[C@@H](CC=2NC=NC=2)C(=O)N1)=O)NC(=O)[C@@H](NC(C)=O)CCCC)C(N)=O)C1=CC=CC=C1 JDKLPDJLXHXHNV-MFVUMRCOSA-N 0.000 description 2
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
IVVNZDGDKPTYHK-JTQLQIEISA-N 1-cyano-2-[(2s)-3,3-dimethylbutan-2-yl]-3-pyridin-4-ylguanidine Chemical compound CC(C)(C)[C@H](C)N=C(NC#N)NC1=CC=NC=C1 IVVNZDGDKPTYHK-JTQLQIEISA-N 0.000 description 2
DPOINJQWXDTOSF-DODZYUBVSA-N 13,14-Dihydro PGE1 Chemical compound CCCCC[C@H](O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O DPOINJQWXDTOSF-DODZYUBVSA-N 0.000 description 2
PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 2
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
OWNWMOPLKWEDCE-UHFFFAOYSA-N 3-(6-methyl-4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CC(C)OC1C1=CC=CC(O)=C1 OWNWMOPLKWEDCE-UHFFFAOYSA-N 0.000 description 2
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
NALVGTOMKSKFFV-UHFFFAOYSA-N 4-fluoro-3-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1F NALVGTOMKSKFFV-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
108060003345 Adrenergic Receptor Proteins 0.000 description 2
102000017910 Adrenergic receptor Human genes 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
208000000044 Amnesia Diseases 0.000 description 2
208000031091 Amnestic disease Diseases 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
102000004414 Calcitonin Gene-Related Peptide Human genes 0.000 description 2
108090000932 Calcitonin Gene-Related Peptide Proteins 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 2
101150049660 DRD2 gene Proteins 0.000 description 2
101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
229940087102 Dopamine D3 receptor agonist Drugs 0.000 description 2
101150097070 Drd3 gene Proteins 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
241001313288 Labia Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
108090000028 Neprilysin Proteins 0.000 description 2
102000003729 Neprilysin Human genes 0.000 description 2
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
102400000050 Oxytocin Human genes 0.000 description 2
101800000989 Oxytocin Proteins 0.000 description 2
101150098694 PDE5A gene Proteins 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
229940127315 Potassium Channel Openers Drugs 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
102000007637 Soluble Guanylyl Cyclase Human genes 0.000 description 2
108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 2
102000012088 Vasoactive Intestinal Peptide Receptors Human genes 0.000 description 2
108010075974 Vasoactive Intestinal Peptide Receptors Proteins 0.000 description 2
OZPWNCNLFBVVEN-RFYLDXRNSA-N [(6s,8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate;[(9s,13s,14s)-13-methyl-17-oxo-9,11,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate;[(8r,9 Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1.OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1.OS(=O)(=O)OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1.C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 OZPWNCNLFBVVEN-RFYLDXRNSA-N 0.000 description 2
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000002160 alpha blocker Substances 0.000 description 2
229960000711 alprostadil Drugs 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
230000006986 amnesia Effects 0.000 description 2
230000001746 atrial effect Effects 0.000 description 2
108010006060 aviptadil Proteins 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000006143 cell culture medium Substances 0.000 description 2
230000003833 cell viability Effects 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
230000019771 cognition Effects 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
239000013058 crude material Substances 0.000 description 2
238000005138 cryopreservation Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000007405 data analysis Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
239000002027 dichloromethane extract Substances 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
XRKMNJXYOFSTBE-UHFFFAOYSA-N disodium;iron(4+);nitroxyl anion;pentacyanide;dihydrate Chemical compound O.O.[Na+].[Na+].[Fe+4].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] XRKMNJXYOFSTBE-UHFFFAOYSA-N 0.000 description 2
230000009429 distress Effects 0.000 description 2
239000002298 dopamine 3 receptor stimulating agent Substances 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000010491 emotional process Effects 0.000 description 2
230000002124 endocrine Effects 0.000 description 2
210000003038 endothelium Anatomy 0.000 description 2
238000011067 equilibration Methods 0.000 description 2
230000001856 erectile effect Effects 0.000 description 2
229960003133 ergot alkaloid Drugs 0.000 description 2
210000001752 female genitalia Anatomy 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
239000012737 fresh medium Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
229960003711 glyceryl trinitrate Drugs 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
239000003999 initiator Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
238000011835 investigation Methods 0.000 description 2
238000010902 jet-milling Methods 0.000 description 2
GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 description 2
238000012417 linear regression Methods 0.000 description 2
229960002006 linsidomine Drugs 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
239000006210 lotion Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
210000000260 male genitalia Anatomy 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
229960002985 medroxyprogesterone acetate Drugs 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
239000003595 mist Substances 0.000 description 2
229960004027 molsidomine Drugs 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
230000001272 neurogenic effect Effects 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
239000002840 nitric oxide donor Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229960002748 norepinephrine Drugs 0.000 description 2
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
230000007310 pathophysiology Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
210000004197 pelvis Anatomy 0.000 description 2
210000003899 penis Anatomy 0.000 description 2
229940066842 petrolatum Drugs 0.000 description 2
229960002310 pinacidil Drugs 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
230000008569 process Effects 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
230000009696 proliferative response Effects 0.000 description 2
239000003380 propellant Substances 0.000 description 2
230000001107 psychogenic effect Effects 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000000700 radioactive tracer Substances 0.000 description 2
229940044601 receptor agonist Drugs 0.000 description 2
239000000018 receptor agonist Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
230000036299 sexual function Effects 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229940083618 sodium nitroprusside Drugs 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
238000003860 storage Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
230000009466 transformation Effects 0.000 description 2
238000000844 transformation Methods 0.000 description 2
230000008733 trauma Effects 0.000 description 2
229960003991 trazodone Drugs 0.000 description 2
PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
210000001215 vagina Anatomy 0.000 description 2
239000003071 vasodilator agent Substances 0.000 description 2
230000035899 viability Effects 0.000 description 2
230000004400 visual pathway Effects 0.000 description 2
210000000239 visual pathway Anatomy 0.000 description 2
238000005406 washing Methods 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
YBHMPNRDOVPQIN-UHFFFAOYSA-N (13E,15S)-15-Hydroxy-9-oxo-8(12),13-prostadienoic acid Natural products CCCCCC(O)C=CC1=C(CCCCCCC(O)=O)C(=O)CC1 YBHMPNRDOVPQIN-UHFFFAOYSA-N 0.000 description 1
BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 1
OBNYTSBDMKGLIN-NUHJPDEHSA-N (2s)-2-[[2-(6-aminopyridin-3-yl)-2-hydroxyethyl]-propylamino]propan-1-ol Chemical compound CCCN([C@@H](C)CO)CC(O)C1=CC=C(N)N=C1 OBNYTSBDMKGLIN-NUHJPDEHSA-N 0.000 description 1
YSUBQYRZZFVMTL-YNDGFOBUSA-N (2s,5r,6r)-6-[[(2r)-2-[[3-[(e)-furan-2-ylmethylideneamino]-2-oxoimidazolidine-1-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)N(C1=O)CCN1\N=C\C1=CC=CO1 YSUBQYRZZFVMTL-YNDGFOBUSA-N 0.000 description 1
XUKUURHRXDUEBC-SVBPBHIXSA-N (3s,5s)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@H](O)C[C@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-SVBPBHIXSA-N 0.000 description 1
FZEDGSMVRLKUOQ-UHFFFAOYSA-N (4-fluoro-3-methoxyphenyl)methanol Chemical compound COC1=CC(CO)=CC=C1F FZEDGSMVRLKUOQ-UHFFFAOYSA-N 0.000 description 1
XOAOLHWGLYYCBQ-SFVWDYPZSA-N (5s)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholin-2-ol Chemical compound O1C[C@H](C)N(CCC)CC1(O)C1=CC=CC(OC)=C1 XOAOLHWGLYYCBQ-SFVWDYPZSA-N 0.000 description 1
SBFGGDZPMSLDMQ-SFVWDYPZSA-N (5s)-2-(3-methoxyphenyl)-5-methyl-4-propylmorpholine Chemical compound O1C[C@H](C)N(CCC)CC1C1=CC=CC(OC)=C1 SBFGGDZPMSLDMQ-SFVWDYPZSA-N 0.000 description 1
ONEKWEYEMWQCHS-UCFFOFKASA-N (5s)-2-[6-(2,5-dimethylpyrrol-1-yl)pyridin-3-yl]-5-methyl-4-propylmorpholin-2-ol Chemical compound O1C[C@H](C)N(CCC)CC1(O)C1=CC=C(N2C(=CC=C2C)C)N=C1 ONEKWEYEMWQCHS-UCFFOFKASA-N 0.000 description 1
LHTRQMBCJMJKCX-ZETCQYMHSA-N (5s)-5-methyl-4-propylmorpholin-2-one Chemical compound CCCN1CC(=O)OC[C@@H]1C LHTRQMBCJMJKCX-ZETCQYMHSA-N 0.000 description 1
XUKAVPATXGYVKJ-WPKBUWHJSA-N (6ar,9r)-n-[(2s)-1-hydroxypropan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CN(C)C3=C1 XUKAVPATXGYVKJ-WPKBUWHJSA-N 0.000 description 1
YUSCRGFYKCAQHE-HQFNMCNFSA-N (8r,9s,13s,14s,17s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol;(8r,9s,13s,14s,16r,17r)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1.OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 YUSCRGFYKCAQHE-HQFNMCNFSA-N 0.000 description 1
BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 description 1
PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 1
FYBFDIIAPRHIQS-KKBLUXBBSA-N (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-thiophen-3-yloxybut-1-enyl]cyclopentyl]hept-5-enoic acid Chemical compound C([C@H](O)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(O)=O)OC=1C=CSC=1 FYBFDIIAPRHIQS-KKBLUXBBSA-N 0.000 description 1
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
HCECSCMCDGLYFU-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-2-(propylamino)ethanol Chemical compound CCCNCC(O)C1=CC(OC)=CC(OC)=C1 HCECSCMCDGLYFU-UHFFFAOYSA-N 0.000 description 1
YXXKQOFSTLERAJ-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-(propylamino)ethanol Chemical compound CCCNCC(O)C1=CC=CC(OC)=C1 YXXKQOFSTLERAJ-UHFFFAOYSA-N 0.000 description 1
USTOOWLKDFWWMN-UHFFFAOYSA-N 1-(4-fluoro-3-methoxyphenyl)-2-(propylamino)ethanol Chemical compound CCCNCC(O)C1=CC=C(F)C(OC)=C1 USTOOWLKDFWWMN-UHFFFAOYSA-N 0.000 description 1
RKEBQLVAZSZKLE-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)-2-(propylamino)ethanol Chemical compound C1=CC(C(O)CNCCC)=CC=C1OCC1=CC=CC=C1 RKEBQLVAZSZKLE-UHFFFAOYSA-N 0.000 description 1
UOTMYNBWXDUBNX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolin-2-ium;chloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 UOTMYNBWXDUBNX-UHFFFAOYSA-N 0.000 description 1
QUUJQFQTLSFCKW-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-chloroquinazolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(Cl)C=C2)C2=N1 QUUJQFQTLSFCKW-UHFFFAOYSA-N 0.000 description 1
OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
BRBNVIXMODBSND-UHFFFAOYSA-N 1-methyl-5-[5-(2-morpholin-4-ylacetyl)-2-propoxyphenyl]-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1=C(C=2NC(=O)C=3N(C)N=C(CCC)C=3N=2)C(OCCC)=CC=C1C(=O)CN1CCOCC1 BRBNVIXMODBSND-UHFFFAOYSA-N 0.000 description 1
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 1
PPYRMVKHPFIXEU-BAKUXOMWSA-N 19-hydroxy-PGB2 Chemical compound CC(O)CCC[C@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1 PPYRMVKHPFIXEU-BAKUXOMWSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
FSKYZRCACCHDGR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-4-one Chemical class C1=CN=C2C(=O)N=CNC2=C1 FSKYZRCACCHDGR-UHFFFAOYSA-N 0.000 description 1
XGHBKRKXZTUREB-UHFFFAOYSA-N 2-(2,5-dimethylpyrrol-1-yl)-5-(oxiran-2-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(C2OC2)C=N1 XGHBKRKXZTUREB-UHFFFAOYSA-N 0.000 description 1
VVUYKKHDKURKHH-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C1=CC(OC)=CC(OC)=C1 VVUYKKHDKURKHH-UHFFFAOYSA-N 0.000 description 1
WCFNRADDDOVFAG-UHFFFAOYSA-N 2-(3-bromo-4-phenylmethoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C(C=C1Br)=CC=C1OCC1=CC=CC=C1 WCFNRADDDOVFAG-UHFFFAOYSA-N 0.000 description 1
BLVMMLMFXYKMPX-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C1=CC=CC(OC)=C1 BLVMMLMFXYKMPX-UHFFFAOYSA-N 0.000 description 1
RDLVEIWWMLUWNF-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-methyl-4-propylmorpholine Chemical compound C1N(CCC)CC(C)OC1C1=CC=CC(OC)=C1 RDLVEIWWMLUWNF-UHFFFAOYSA-N 0.000 description 1
WZGRAZZOCGLUHH-UHFFFAOYSA-N 2-(4-chloro-3-methoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C1=CC=C(Cl)C(OC)=C1 WZGRAZZOCGLUHH-UHFFFAOYSA-N 0.000 description 1
ZTAQBNKZCRIMNG-UHFFFAOYSA-N 2-(4-fluoro-3-methoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C1=CC=C(F)C(OC)=C1 ZTAQBNKZCRIMNG-UHFFFAOYSA-N 0.000 description 1
AUUDNCBDZHBKMP-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CCOC1C(C=C1)=CC=C1OCC1=CC=CC=C1 AUUDNCBDZHBKMP-UHFFFAOYSA-N 0.000 description 1
YQMQTEJARSWZPZ-UHFFFAOYSA-N 2-amino-1-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC(C(O)CN)=C1 YQMQTEJARSWZPZ-UHFFFAOYSA-N 0.000 description 1
LBNVNODDDSSXCY-UHFFFAOYSA-N 2-amino-1-(4-chloro-3-methoxyphenyl)ethanol Chemical compound COC1=CC(C(O)CN)=CC=C1Cl LBNVNODDDSSXCY-UHFFFAOYSA-N 0.000 description 1
RJYCTAQEHBSFSH-UHFFFAOYSA-N 2-amino-1-(4-fluoro-3-methoxyphenyl)ethanol Chemical compound COC1=CC(C(O)CN)=CC=C1F RJYCTAQEHBSFSH-UHFFFAOYSA-N 0.000 description 1
YZOUUVUNKGUDSK-UHFFFAOYSA-N 2-amino-1-(4-phenylmethoxyphenyl)ethanol Chemical compound C1=CC(C(O)CN)=CC=C1OCC1=CC=CC=C1 YZOUUVUNKGUDSK-UHFFFAOYSA-N 0.000 description 1
IOOHBIFQNQQUFI-UHFFFAOYSA-N 2-bromo-1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(=O)CBr)=C1 IOOHBIFQNQQUFI-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
SCOJKGRNQDKFRP-UHFFFAOYSA-N 2-chloro-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CCl SCOJKGRNQDKFRP-UHFFFAOYSA-N 0.000 description 1
XNOYVTCERVOCMV-UHFFFAOYSA-N 2-ethyl-6-(3-methoxyphenyl)-4-propylmorpholin-3-one Chemical compound O1C(CC)C(=O)N(CCC)CC1C1=CC=CC(OC)=C1 XNOYVTCERVOCMV-UHFFFAOYSA-N 0.000 description 1
XWIFREIAHMOYEZ-UHFFFAOYSA-N 2-ethyl-6-(3-methoxyphenyl)-4-propylmorpholine Chemical compound C1N(CCC)CC(CC)OC1C1=CC=CC(OC)=C1 XWIFREIAHMOYEZ-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
VXODQPFBRCBUSW-UHFFFAOYSA-N 2-nitro-4-(4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CCOC1C1=CC=C(O)C([N+]([O-])=O)=C1 VXODQPFBRCBUSW-UHFFFAOYSA-N 0.000 description 1
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
PPWLAQVKIFDULF-UHFFFAOYSA-N 2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C=C1C1=CC=CC=C1 PPWLAQVKIFDULF-UHFFFAOYSA-N 0.000 description 1
JXZZEXZZKAWDSP-UHFFFAOYSA-N 3-(2-(4-Benzamidopiperid-1-yl)ethyl)indole Chemical compound C1CN(CCC=2C3=CC=CC=C3NC=2)CCC1NC(=O)C1=CC=CC=C1 JXZZEXZZKAWDSP-UHFFFAOYSA-N 0.000 description 1
NARNOSPCARRMAR-UHFFFAOYSA-N 3-(6-ethyl-4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CC(CC)OC1C1=CC=CC(O)=C1 NARNOSPCARRMAR-UHFFFAOYSA-N 0.000 description 1
SBHNNNRQZGYOAU-YVEFUNNKSA-N 3-[(6ar,9s)-5-bromo-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=C(Br)NC3=C1 SBHNNNRQZGYOAU-YVEFUNNKSA-N 0.000 description 1
FCRJELOYDVBTGW-ILZDJORESA-N 3-[(6ar,9s,10ar)-7-propyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)CCC)NC(=O)N(CC)CC)=C3C2=CNC3=C1 FCRJELOYDVBTGW-ILZDJORESA-N 0.000 description 1
ZEDCOUIRGFQKTH-UHFFFAOYSA-N 3-acetyl-1-[(2-chlorophenyl)methyl]-2-propylindole-6-carboxylic acid Chemical compound CCCC1=C(C(C)=O)C2=CC=C(C(O)=O)C=C2N1CC1=CC=CC=C1Cl ZEDCOUIRGFQKTH-UHFFFAOYSA-N 0.000 description 1
SISGKOAGBAJWPA-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-(2-methylpropoxy)pyridin-3-yl]-2-(1-methylpiperidin-4-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CN=C(OCC(C)C)C(C=2NC(=O)C3=NN(C(CC)=C3N=2)C2CCN(C)CC2)=C1 SISGKOAGBAJWPA-UHFFFAOYSA-N 0.000 description 1
WKISNFXGTYNPOO-OAHLLOKOSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-[(2r)-1-methoxypropan-2-yl]oxypyridin-3-yl]-2-methyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CN=C(O[C@H](C)COC)C(C=2NC(=O)C3=NN(C)C(CC)=C3N=2)=C1 WKISNFXGTYNPOO-OAHLLOKOSA-N 0.000 description 1
NIBCDDKWFDEBEP-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-2-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC1=C2CC)=NC(=O)C1=NN2CC1=CC=CC=N1 NIBCDDKWFDEBEP-UHFFFAOYSA-N 0.000 description 1
NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 1
ZRFWHHCXSSACAW-UHFFFAOYSA-M 3-morpholin-4-yloxadiazol-3-ium-5-amine;chloride Chemical compound [Cl-].O1C(N)=C[N+](N2CCOCC2)=N1 ZRFWHHCXSSACAW-UHFFFAOYSA-M 0.000 description 1
IZHCCKWRFAIIPH-UHFFFAOYSA-N 4-(4-propylmorpholin-2-yl)phenol Chemical compound C1N(CCC)CCOC1C1=CC=C(O)C=C1 IZHCCKWRFAIIPH-UHFFFAOYSA-N 0.000 description 1
BMUKKTUHUDJSNZ-UHFFFAOYSA-N 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C(C)NC(C)COC1=CC=CC=C1 BMUKKTUHUDJSNZ-UHFFFAOYSA-N 0.000 description 1
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 1
INLBUQIADGPECI-UHFFFAOYSA-N 5-(5-acetyl-2-butoxypyridin-3-yl)-3-ethyl-2-(1-ethylazetidin-3-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCCOC1=NC=C(C(C)=O)C=C1C1=NC2=C(CC)N(C3CN(CC)C3)N=C2C(=O)N1 INLBUQIADGPECI-UHFFFAOYSA-N 0.000 description 1
SUNRSIDIGUGCSU-UHFFFAOYSA-N 5-(5-acetyl-2-propoxypyridin-3-yl)-3-ethyl-2-(1-propan-2-ylazetidin-3-yl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=NC=C(C(C)=O)C=C1C1=NC2=C(CC)N(C3CN(C3)C(C)C)N=C2C(=O)N1 SUNRSIDIGUGCSU-UHFFFAOYSA-N 0.000 description 1
108091005477 5-HT3 receptors Proteins 0.000 description 1
108091005435 5-HT6 receptors Proteins 0.000 description 1
NMEFXGPLRHHGTK-UHFFFAOYSA-N 5-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylpyridin-3-yl]-3-ethyl-2-phenyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCOC1=NC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC(=O)C1=N2)=NC1=C(CC)N2C1=CC=CC=C1 NMEFXGPLRHHGTK-UHFFFAOYSA-N 0.000 description 1
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
QPBXXHOQSFVUKL-UHFFFAOYSA-N 5-bromo-3-[3-(4-chlorophenyl)propoxy]-4-(pyridin-2-ylmethylamino)-1h-pyridazin-6-one Chemical compound C1=CC(Cl)=CC=C1CCCOC1=NNC(=O)C(Br)=C1NCC1=CC=CC=N1 QPBXXHOQSFVUKL-UHFFFAOYSA-N 0.000 description 1
YJMYSLFFZJUXOA-UHFFFAOYSA-N 5-bromo-3-[3-(4-chlorophenyl)propoxy]-4-(pyridin-3-ylmethylamino)-1h-pyridazin-6-one Chemical compound C1=CC(Cl)=CC=C1CCCOC1=NNC(=O)C(Br)=C1NCC1=CC=CN=C1 YJMYSLFFZJUXOA-UHFFFAOYSA-N 0.000 description 1
WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
PHRZFJNZFGXHQS-UHFFFAOYSA-N 6-(3,5-dimethoxyphenyl)-4-propylmorpholin-3-one Chemical compound O1CC(=O)N(CCC)CC1C1=CC(OC)=CC(OC)=C1 PHRZFJNZFGXHQS-UHFFFAOYSA-N 0.000 description 1
CEAIARPCLHBMPG-UHFFFAOYSA-N 6-(3-methoxyphenyl)-2-methyl-4-propylmorpholin-3-one Chemical compound O1C(C)C(=O)N(CCC)CC1C1=CC=CC(OC)=C1 CEAIARPCLHBMPG-UHFFFAOYSA-N 0.000 description 1
UMRILYSMEDJJOG-UHFFFAOYSA-N 6-(3-methoxyphenyl)-4-propylmorpholin-3-one Chemical compound O1CC(=O)N(CCC)CC1C1=CC=CC(OC)=C1 UMRILYSMEDJJOG-UHFFFAOYSA-N 0.000 description 1
WHTKKFJNNCGJKL-UHFFFAOYSA-N 6-(4-chloro-3-methoxyphenyl)-4-propylmorpholin-3-one Chemical compound O1CC(=O)N(CCC)CC1C1=CC=C(Cl)C(OC)=C1 WHTKKFJNNCGJKL-UHFFFAOYSA-N 0.000 description 1
IVJMNLODVNTXFE-UHFFFAOYSA-N 6-(4-fluoro-3-methoxyphenyl)-4-propylmorpholin-3-one Chemical compound O1CC(=O)N(CCC)CC1C1=CC=C(F)C(OC)=C1 IVJMNLODVNTXFE-UHFFFAOYSA-N 0.000 description 1
VCCNKWWXYVWTLT-CYZBKYQRSA-N 7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCCNKWWXYVWTLT-CYZBKYQRSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010002261 Androgen deficiency Diseases 0.000 description 1
206010002652 Anorgasmia Diseases 0.000 description 1
206010003439 Artificial menopause Diseases 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
102100036465 Autoimmune regulator Human genes 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
201000004569 Blindness Diseases 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
101100135858 Caenorhabditis elegans pde-2 gene Proteins 0.000 description 1
101100135867 Caenorhabditis elegans pde-3 gene Proteins 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
102000018208 Cannabinoid Receptor Human genes 0.000 description 1
108050007331 Cannabinoid receptor Proteins 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
108091006146 Channels Proteins 0.000 description 1
108010023798 Charybdotoxin Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
241000699802 Cricetulus griseus Species 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
102000004654 Cyclic GMP-Dependent Protein Kinases Human genes 0.000 description 1
108010003591 Cyclic GMP-Dependent Protein Kinases Proteins 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
206010011878 Deafness Diseases 0.000 description 1
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
101100135859 Dictyostelium discoideum regA gene Proteins 0.000 description 1
102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 description 1
108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 1
208000004483 Dyspareunia Diseases 0.000 description 1
201000009273 Endometriosis Diseases 0.000 description 1
108010059378 Endopeptidases Proteins 0.000 description 1
102000005593 Endopeptidases Human genes 0.000 description 1
102000010180 Endothelin receptor Human genes 0.000 description 1
108050001739 Endothelin receptor Proteins 0.000 description 1
241001492222 Epicoccum Species 0.000 description 1
IHPHPGLJYCDONF-UHFFFAOYSA-N Essigsaeure-propylamid Natural products CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
101150104779 HTR2A gene Proteins 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
102000007625 Hirudins Human genes 0.000 description 1
108010007267 Hirudins Proteins 0.000 description 1
101000928549 Homo sapiens Autoimmune regulator Proteins 0.000 description 1
101000865224 Homo sapiens D(3) dopamine receptor Proteins 0.000 description 1
101150013372 Htr2c gene Proteins 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
206010020850 Hyperthyroidism Diseases 0.000 description 1
208000001953 Hypotension 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
206010061216 Infarction Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
229940122355 Insulin sensitizer Drugs 0.000 description 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229940117029 Melanocortin receptor agonist Drugs 0.000 description 1
108010008364 Melanocortins Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
FQWRAVYMZULPNK-UHFFFAOYSA-N N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine Chemical compound OC(=O)C(N)CCCNC(N)=NO FQWRAVYMZULPNK-UHFFFAOYSA-N 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
HRRBJVNMSRJFHQ-UHFFFAOYSA-N Naftopidil Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C3=CC=CC=C3C=CC=2)CC1 HRRBJVNMSRJFHQ-UHFFFAOYSA-N 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
101710138657 Neurotoxin Proteins 0.000 description 1
YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000000006 Nitroglycerin Substances 0.000 description 1
102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 1
108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 1
229940121954 Opioid receptor agonist Drugs 0.000 description 1
229940123257 Opioid receptor antagonist Drugs 0.000 description 1
102000004279 Oxytocin receptors Human genes 0.000 description 1
108090000876 Oxytocin receptors Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
244000131316 Panax pseudoginseng Species 0.000 description 1
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
208000029082 Pelvic Inflammatory Disease Diseases 0.000 description 1
TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
239000000026 Pentaerythritol tetranitrate Substances 0.000 description 1
QZVCTJOXCFMACW-UHFFFAOYSA-N Phenoxybenzamine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)COC1=CC=CC=C1 QZVCTJOXCFMACW-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
229940121828 Phosphodiesterase 2 inhibitor Drugs 0.000 description 1
229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
101100082606 Plasmodium falciparum (isolate 3D7) PDEbeta gene Proteins 0.000 description 1
208000005374 Poisoning Diseases 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000002500 Primary Ovarian Insufficiency Diseases 0.000 description 1
102000003946 Prolactin Human genes 0.000 description 1
108010057464 Prolactin Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 1
101100135860 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PDE2 gene Proteins 0.000 description 1
102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 1
108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
208000029033 Spinal Cord disease Diseases 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 1
JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 description 1
108010022394 Threonine synthase Proteins 0.000 description 1
229940122388 Thrombin inhibitor Drugs 0.000 description 1
102100038388 Vasoactive intestinal polypeptide receptor 1 Human genes 0.000 description 1
101710137655 Vasoactive intestinal polypeptide receptor 1 Proteins 0.000 description 1
102000004136 Vasopressin Receptors Human genes 0.000 description 1
108090000643 Vasopressin Receptors Proteins 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
MMPCMJGFURZYOY-WRWLIDTKSA-N [(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl azepane-1-carboxylate Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)OC(=O)N1CCCCCC1 MMPCMJGFURZYOY-WRWLIDTKSA-N 0.000 description 1
TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
RQBGLYREDLMZMC-UHFFFAOYSA-N [N].C1COCCN1 Chemical compound [N].C1COCCN1 RQBGLYREDLMZMC-UHFFFAOYSA-N 0.000 description 1
ANZIISNSHPKVRV-UHFFFAOYSA-N abanoquil Chemical compound C1=C(OC)C(OC)=CC2=NC(N3CCC=4C=C(C(=CC=4C3)OC)OC)=CC(N)=C21 ANZIISNSHPKVRV-UHFFFAOYSA-N 0.000 description 1
229950010137 abanoquil Drugs 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
VPXSOMITANBBPE-XGWLTEMNSA-N acetergamine Chemical compound C1=CC=C2[C@H]3C[C@@H](CNC(C)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 VPXSOMITANBBPE-XGWLTEMNSA-N 0.000 description 1
229950004701 acetergamine Drugs 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000008484 agonism Effects 0.000 description 1
229960004607 alfuzosin Drugs 0.000 description 1
WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 description 1
108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 1
102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 1
229960000528 amlodipine Drugs 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 description 1
210000003484 anatomy Anatomy 0.000 description 1
229960003473 androstanolone Drugs 0.000 description 1
229940127282 angiotensin receptor antagonist Drugs 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000000702 anti-platelet effect Effects 0.000 description 1
239000003529 anticholesteremic agent Substances 0.000 description 1
229940127226 anticholesterol agent Drugs 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000001623 arteriogenic effect Effects 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
SHZPNDRIDUBNMH-NIJVSVLQSA-L atorvastatin calcium trihydrate Chemical compound O.O.O.[Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 SHZPNDRIDUBNMH-NIJVSVLQSA-L 0.000 description 1
229950000586 aviptadil Drugs 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000006399 behavior Effects 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000036770 blood supply Effects 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
229950010062 brazergoline Drugs 0.000 description 1
FFHBJDQSGDNCIV-MFVUMRCOSA-N bremelanotide Chemical compound C([C@@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCNC(=O)C[C@@H](C(N[C@@H](CC=2NC=NC=2)C(=O)N1)=O)NC(=O)[C@@H](NC(C)=O)CCCC)C(O)=O)C1=CC=CC=C1 FFHBJDQSGDNCIV-MFVUMRCOSA-N 0.000 description 1
229950006651 bromerguride Drugs 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
229960001058 bupropion Drugs 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
QTAOMKOIBXZKND-PPHPATTJSA-N carbidopa Chemical compound O.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 QTAOMKOIBXZKND-PPHPATTJSA-N 0.000 description 1
229960004205 carbidopa Drugs 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
UMMADZJLZAPZAW-OVXHCKHTSA-N carboprost tromethamine Chemical compound OCC([NH3+])(CO)CO.CCCCC[C@](C)(O)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC([O-])=O UMMADZJLZAPZAW-OVXHCKHTSA-N 0.000 description 1
229960005296 carboprost tromethamine Drugs 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229940062399 cenestin Drugs 0.000 description 1
229940081733 cetearyl alcohol Drugs 0.000 description 1
230000035606 childbirth Effects 0.000 description 1
210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
239000000544 cholinesterase inhibitor Substances 0.000 description 1
235000019504 cigarettes Nutrition 0.000 description 1
230000004087 circulation Effects 0.000 description 1
DYIUKMSMAJWWAT-NEPJUHHUSA-N cis-2-hexyl-5-methyl-3,4,5,6a,7,8,9,9a-octahydrocyclopent[4,5]-imidazo[2, 1-b]purin-4-one Chemical compound N([C@@H]1CCC[C@@H]1N12)=C1N(C)C(=O)C1=C2NC(CCCCCC)=N1 DYIUKMSMAJWWAT-NEPJUHHUSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
208000018912 cluster headache syndrome Diseases 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000000056 copulatory effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
238000002447 crystallographic data Methods 0.000 description 1
CNVQLPPZGABUCM-LIGYZCPXSA-N ctx toxin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@H]3CSSC[C@@H](C(N[C@@H](CC=4C5=CC=CC=C5NC=4)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CCCNC(N)=N)NC3=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CO)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3NC=NC=3)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N2)C(C)C)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)O)NC1=O)=O)CCSC)C(C)C)[C@@H](C)O)NC(=O)[C@H]1NC(=O)CC1)C1=CC=CC=C1 CNVQLPPZGABUCM-LIGYZCPXSA-N 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
229960000729 cyclandelate Drugs 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
229960002947 dapiprazole Drugs 0.000 description 1
RFWZESUMWJKKRN-UHFFFAOYSA-N dapiprazole Chemical compound CC1=CC=CC=C1N1CCN(CCC=2N3CCCCC3=NN=2)CC1 RFWZESUMWJKKRN-UHFFFAOYSA-N 0.000 description 1
DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
KWDSFGYQALRPMG-UHFFFAOYSA-N delta-N-Hydroxy-L-orginin Natural products OC(=O)C(N)CCCN(O)C(N)=N KWDSFGYQALRPMG-UHFFFAOYSA-N 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
229960003914 desipramine Drugs 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-O diazenium Chemical compound [NH2+]=N RAABOESOVLLHRU-UHFFFAOYSA-O 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
230000010339 dilation Effects 0.000 description 1
229960001342 dinoprost Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229960001389 doxazosin Drugs 0.000 description 1
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
229940000406 drug candidate Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
229940126534 drug product Drugs 0.000 description 1
229940112141 dry powder inhaler Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
210000000750 endocrine system Anatomy 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
YREISLCRUMOYAY-IIPCNOPRSA-N ergometrine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 YREISLCRUMOYAY-IIPCNOPRSA-N 0.000 description 1
229940030804 ergonovine maleate Drugs 0.000 description 1
229960001903 ergotamine tartrate Drugs 0.000 description 1
SNFOERUNNSHUGP-ZXZARUISSA-N erythrityl tetranitrate Chemical compound [O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@@H](O[N+]([O-])=O)CO[N+]([O-])=O SNFOERUNNSHUGP-ZXZARUISSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940064258 estrace Drugs 0.000 description 1
229940098618 estring Drugs 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
239000002834 estrogen receptor modulator Substances 0.000 description 1
JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000013265 extended release Methods 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
230000006870 function Effects 0.000 description 1
230000005714 functional activity Effects 0.000 description 1
238000011990 functional testing Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
KYBOHGVERHWSSV-VNIVIJDLSA-N gemeprost Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC\C=C\C(=O)OC KYBOHGVERHWSSV-VNIVIJDLSA-N 0.000 description 1
229960003480 gemeprost Drugs 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
229960004580 glibenclamide Drugs 0.000 description 1
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
229960001381 glipizide Drugs 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
229940049654 glyceryl behenate Drugs 0.000 description 1
230000002710 gonadal effect Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
229940006607 hirudin Drugs 0.000 description 1
WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
229940126904 hypoglycaemic agent Drugs 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000002267 hypothalamic effect Effects 0.000 description 1
210000003016 hypothalamus Anatomy 0.000 description 1
230000002989 hypothyroidism Effects 0.000 description 1
208000003532 hypothyroidism Diseases 0.000 description 1
229950001476 idazoxan Drugs 0.000 description 1
HPMRFMKYPGXPEP-UHFFFAOYSA-N idazoxan Chemical compound N1CCN=C1C1OC2=CC=CC=C2OC1 HPMRFMKYPGXPEP-UHFFFAOYSA-N 0.000 description 1
239000007943 implant Substances 0.000 description 1
229960002056 indoramin Drugs 0.000 description 1
230000007574 infarction Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000030214 innervation Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
108010024941 iodothyronine deiodinase type II Proteins 0.000 description 1
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
229960000201 isosorbide dinitrate Drugs 0.000 description 1
YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
229960003827 isosorbide mononitrate Drugs 0.000 description 1
229960004819 isoxsuprine Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
PRFXRIUZNKLRHM-UHFFFAOYSA-N l-prostaglandin B2 Natural products CCCCCC(O)C=CC1=C(CC=CCCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-UHFFFAOYSA-N 0.000 description 1
230000006651 lactation Effects 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
230000001983 lactogenic effect Effects 0.000 description 1
229960002367 lasofoxifene Drugs 0.000 description 1
235000005772 leucine Nutrition 0.000 description 1
FKDHHVKWGRFRTG-UHFFFAOYSA-N linsidomine Chemical compound [N-]1OC(=N)C=[N+]1N1CCOCC1 FKDHHVKWGRFRTG-UHFFFAOYSA-N 0.000 description 1
229940002661 lipitor Drugs 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
229960004773 losartan Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229950002454 lysergide Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000007726 management method Methods 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960004616 medroxyprogesterone Drugs 0.000 description 1
239000002865 melanocortin Substances 0.000 description 1
239000000336 melanocortin receptor agonist Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
229960004650 metergoline Drugs 0.000 description 1
SZUQJDJBJHBVBO-CTTKVJGISA-N metergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C=3C=CC=C4N(C)C=C(C=34)C2)=C1)C)C1=CC=CC=C1 SZUQJDJBJHBVBO-CTTKVJGISA-N 0.000 description 1
229950004958 metergotamine Drugs 0.000 description 1
IYUKFAFDFHZKPI-DFWYDOINSA-N methyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](C)N IYUKFAFDFHZKPI-DFWYDOINSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
MXELDPKESKXREN-UHFFFAOYSA-N methyl 5-[3-(4,4-diphenylpiperidin-1-yl)propylcarbamoyl]-2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)NCCCN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=C([N+]([O-])=O)C=C1 MXELDPKESKXREN-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229960001566 methyltestosterone Drugs 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
229960003632 minoxidil Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
229950005705 naftopidil Drugs 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
230000008693 nausea Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000002581 neurotoxin Substances 0.000 description 1
231100000618 neurotoxin Toxicity 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960003642 nicergoline Drugs 0.000 description 1
229960002497 nicorandil Drugs 0.000 description 1
LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229960003753 nitric oxide Drugs 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
108010020615 nociceptin receptor Proteins 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
230000001129 nonadrenergic effect Effects 0.000 description 1
230000002536 noncholinergic effect Effects 0.000 description 1
230000002474 noradrenergic effect Effects 0.000 description 1
210000001009 nucleus accumben Anatomy 0.000 description 1
210000000869 occipital lobe Anatomy 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
229950000973 omapatrilat Drugs 0.000 description 1
239000003402 opiate agonist Substances 0.000 description 1
239000003401 opiate antagonist Substances 0.000 description 1
210000001328 optic nerve Anatomy 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003539 oral contraceptive agent Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
125000002734 organomagnesium group Chemical group 0.000 description 1
208000015124 ovarian disease Diseases 0.000 description 1
201000004535 ovarian dysfunction Diseases 0.000 description 1
231100000543 ovarian dysfunction Toxicity 0.000 description 1
210000003101 oviduct Anatomy 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000003049 oxytocinergic effect Effects 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
238000002638 palliative care Methods 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
229960003207 papaverine hydrochloride Drugs 0.000 description 1
230000001734 parasympathetic effect Effects 0.000 description 1
210000002963 paraventricular hypothalamic nucleus Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
229960004851 pergolide Drugs 0.000 description 1
YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
208000027232 peripheral nervous system disease Diseases 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229960003418 phenoxybenzamine Drugs 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960003056 phentolamine mesylate Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229940113124 polysorbate 60 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
238000011176 pooling Methods 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229940063238 premarin Drugs 0.000 description 1
206010036601 premature menopause Diseases 0.000 description 1
208000017942 premature ovarian failure 1 Diseases 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000436 pro-erectile effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
229950004866 propisergide Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
BGKHCLZFGPIKKU-LDDQNKHRSA-N prostaglandin A1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O BGKHCLZFGPIKKU-LDDQNKHRSA-N 0.000 description 1
YBHMPNRDOVPQIN-VSOYFRJCSA-N prostaglandin B1 Chemical compound CCCCC[C@H](O)\C=C\C1=C(CCCCCCC(O)=O)C(=O)CC1 YBHMPNRDOVPQIN-VSOYFRJCSA-N 0.000 description 1
PRFXRIUZNKLRHM-HKVRTXJWSA-N prostaglandin B2 Chemical compound CCCCC[C@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1 PRFXRIUZNKLRHM-HKVRTXJWSA-N 0.000 description 1
PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229950007140 proterguride Drugs 0.000 description 1
210000003689 pubic bone Anatomy 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
239000013014 purified material Substances 0.000 description 1
UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical class O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 description 1
239000003227 purinergic agonist Substances 0.000 description 1
210000002637 putamen Anatomy 0.000 description 1
IUYQIJQHYDZUDF-UHFFFAOYSA-N pyrazolo[3,4-d]pyrimidin-4-one Chemical class O=C1N=CN=C2N=NC=C12 IUYQIJQHYDZUDF-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
230000004648 relaxation of smooth muscle Effects 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
JOSMPBVYYKRYLG-OLZOCXBDSA-N sch-51866 Chemical compound N1([C@H]2CCC[C@H]2N=C1N(C(C=1N2)=O)C)C=1N=C2CC1=CC=C(C(F)(F)F)C=C1 JOSMPBVYYKRYLG-OLZOCXBDSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000035807 sensation Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
230000035936 sexual power Effects 0.000 description 1
230000036332 sexual response Effects 0.000 description 1
229960003310 sildenafil Drugs 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
206010042772 syncope Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960002613 tamsulosin Drugs 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229960001693 terazosin Drugs 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960004558 terguride Drugs 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
229950002099 tiaprost Drugs 0.000 description 1
229960002312 tolazoline Drugs 0.000 description 1
JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
230000008736 traumatic injury Effects 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
YNZXWQJZEDLQEG-UHFFFAOYSA-N trimazosin Chemical compound N1=C2C(OC)=C(OC)C(OC)=CC2=C(N)N=C1N1CCN(C(=O)OCC(C)(C)O)CC1 YNZXWQJZEDLQEG-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
206010046947 vaginismus Diseases 0.000 description 1
229960002381 vardenafil Drugs 0.000 description 1
230000004865 vascular response Effects 0.000 description 1
230000002227 vasoactive effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
230000000982 vasogenic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000001720 vestibular Effects 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
230000004393 visual impairment Effects 0.000 description 1
238000012800 visualization Methods 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
229960005080 warfarin Drugs 0.000 description 1
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
229960000317 yohimbine Drugs 0.000 description 1
AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Gynecology & Obstetrics (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Addiction (AREA)
Anesthesiology (AREA)
Psychology (AREA)
Dermatology (AREA)
Hematology (AREA)
Diabetes (AREA)
Child & Adolescent Psychology (AREA)
Pregnancy & Childbirth (AREA)
Nutrition Science (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

NO20052557A 2002-12-10 2005-05-26 Morfolinderivater, preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike for fremstilling av medikament for behandling av sykdom NO330143B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB0228787A GB0228787D0 (en)	2002-12-10	2002-12-10	Morpholine dopamine agonists
GB0308460A GB0308460D0 (en)	2003-04-11	2003-04-11	Morpholine dopamine agonists
GB0313606A GB0313606D0 (en)	2003-06-12	2003-06-12	Morpholine dopamine agonists
PCT/IB2003/005683 WO2004052372A1 (en)	2002-12-10	2003-12-02	Morpholine derivatives for use as dopamine agonists in the treatment of i.a. sexual dysfunction

Publications (3)

Publication Number	Publication Date
NO20052557D0 NO20052557D0 (no)	2005-05-26
NO20052557L NO20052557L (no)	2005-09-06
NO330143B1 true NO330143B1 (no)	2011-02-21

Family

ID=32512061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20052557A NO330143B1 (no)	2002-12-10	2005-05-26	Morfolinderivater, preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike for fremstilling av medikament for behandling av sykdom

Country Status (36)

Country	Link
EP (1)	EP1572214B1 (es)
JP (3)	JP3889775B2 (es)
KR (1)	KR100796102B1 (es)
AP (1)	AP2005003325A0 (es)
AR (1)	AR042339A1 (es)
AT (1)	ATE460938T1 (es)
AU (1)	AU2003302878B2 (es)
CA (1)	CA2508262C (es)
CO (1)	CO5700781A2 (es)
CR (1)	CR7869A (es)
CY (1)	CY1110130T1 (es)
DE (1)	DE60331769D1 (es)
DK (1)	DK1572214T3 (es)
EA (1)	EA009589B1 (es)
EC (1)	ECSP055850A (es)
ES (1)	ES2339767T3 (es)
GE (1)	GEP20074272B (es)
HN (1)	HN2003000401A (es)
HR (1)	HRP20050523A2 (es)
IS (1)	IS7843A (es)
MA (1)	MA27605A1 (es)
MX (1)	MXPA05006151A (es)
MY (1)	MY144338A (es)
NL (1)	NL1024983C2 (es)
NO (1)	NO330143B1 (es)
NZ (1)	NZ540505A (es)
OA (1)	OA13014A (es)
PA (1)	PA8591601A1 (es)
PE (1)	PE20040906A1 (es)
PL (1)	PL377480A1 (es)
PT (1)	PT1572214E (es)
RS (1)	RS51442B (es)
SI (1)	SI1572214T1 (es)
TW (1)	TW200423944A (es)
UY (1)	UY28117A1 (es)
WO (1)	WO2004052372A1 (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4093588B2 (ja) *	2004-05-26	2008-06-04	ファイザー・インク	新規インダゾール及びインドロン誘導体及び調合剤としてのそれらの使用
BRPI0511571A (pt) *	2004-05-27	2008-01-02	Pfizer	derivados de aminopiridina como agonistas de dopamina d3 seletivos
GB0502509D0 (en)	2005-02-07	2005-03-16	Pfizer Ltd	Novel salt form of a dopamine agonist
TW200740779A (en)	2005-07-22	2007-11-01	Mitsubishi Pharma Corp	Intermediate compound for synthesizing pharmaceutical agent and production method thereof
GB0700786D0 (en) *	2007-01-15	2007-02-21	Pfizer Ltd	Morpholine dopamine agonists for the treatment of pain
EP2571859B1 (en)	2010-05-21	2015-07-22	Research Triangle Institute	1-phenylmorpholine derivatives as hydroxybupropion analogues for treating drug dependence
WO2011146850A1 (en) *	2010-05-21	2011-11-24	Research Triangle Institute	Phenylmorpholines and analogues thereof
PL3080284T3 (pl)	2013-12-11	2018-05-30	F.Hoffmann-La Roche Ag	Sposób wytwarzania chiralnej 2-(4-aminofenylo)morfoliny
GB2543296A (en) *	2015-10-13	2017-04-19	Indivior Uk Ltd	Dopamine D3 receptor antagonists having a morpholine moiety
EP3953350A1 (en)	2019-04-12	2022-02-16	The United States of America, as Represented by The Department of Health and Human Services	D3 receptor agonist compounds; methods of preparation; intermediates thereof; and methods of use thereof
EP3725768A1 (en) *	2019-04-17	2020-10-21	Newron Pharmaceuticals S.p.A.	Process for the production of substituted 2-[2-(phenyl) ethylamino]alkaneamide derivatives
CN118684636B (zh) *	2024-05-31	2025-03-11	上海优合贝德医药科技有限公司	一种4-吗啉-1-苯基巯基-2-丁酮的合成工艺

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB851311A (en) *	1958-04-02	1960-10-12	Geigy Ag J R	Morpholine compounds and their production
GB9108629D0 (en) *	1991-04-23	1991-06-12	Wellcome Found	Heterocyclic pharmaceutical compounds,preparation and use
GB0130219D0 (en) *	2001-12-18	2002-02-06	Pfizer Ltd	Compounds for the treatment of sexual dysfunction

2003
- 2003-12-02 EA EA200500801A patent/EA009589B1/ru not_active IP Right Cessation
- 2003-12-02 DK DK03812639.7T patent/DK1572214T3/da active
- 2003-12-02 JP JP2005502342A patent/JP3889775B2/ja not_active Expired - Fee Related
- 2003-12-02 AU AU2003302878A patent/AU2003302878B2/en not_active Ceased
- 2003-12-02 SI SI200331801T patent/SI1572214T1/sl unknown
- 2003-12-02 KR KR1020057010474A patent/KR100796102B1/ko not_active Expired - Fee Related
- 2003-12-02 EP EP03812639A patent/EP1572214B1/en not_active Expired - Lifetime
- 2003-12-02 HR HR20050523A patent/HRP20050523A2/hr not_active Application Discontinuation
- 2003-12-02 AT AT03812639T patent/ATE460938T1/de active
- 2003-12-02 PT PT03812639T patent/PT1572214E/pt unknown
- 2003-12-02 MX MXPA05006151A patent/MXPA05006151A/es active IP Right Grant
- 2003-12-02 AP AP2005003325A patent/AP2005003325A0/xx unknown
- 2003-12-02 ES ES03812639T patent/ES2339767T3/es not_active Expired - Lifetime
- 2003-12-02 CA CA002508262A patent/CA2508262C/en not_active Expired - Fee Related
- 2003-12-02 RS YUP-2005/0445A patent/RS51442B/sr unknown
- 2003-12-02 DE DE60331769T patent/DE60331769D1/de not_active Expired - Lifetime
- 2003-12-02 OA OA1200500171A patent/OA13014A/en unknown
- 2003-12-02 GE GEAP20038838A patent/GEP20074272B/en unknown
- 2003-12-02 WO PCT/IB2003/005683 patent/WO2004052372A1/en not_active Ceased
- 2003-12-02 NZ NZ540505A patent/NZ540505A/en not_active IP Right Cessation
- 2003-12-02 PL PL377480A patent/PL377480A1/pl not_active Application Discontinuation
- 2003-12-05 PE PE2003001234A patent/PE20040906A1/es not_active Application Discontinuation
- 2003-12-08 MY MYPI20034690A patent/MY144338A/en unknown
- 2003-12-09 HN HN2003000401A patent/HN2003000401A/es unknown
- 2003-12-09 AR ARP030104524A patent/AR042339A1/es unknown
- 2003-12-09 TW TW092134694A patent/TW200423944A/zh unknown
- 2003-12-10 PA PA20038591601A patent/PA8591601A1/es unknown
- 2003-12-10 UY UY28117A patent/UY28117A1/es not_active Application Discontinuation
- 2003-12-10 NL NL1024981A patent/NL1024983C2/nl not_active IP Right Cessation
2005
- 2005-05-12 IS IS7843A patent/IS7843A/is unknown
- 2005-05-26 NO NO20052557A patent/NO330143B1/no not_active IP Right Cessation
- 2005-06-10 EC EC2005005850A patent/ECSP055850A/es unknown
- 2005-06-10 CR CR7869A patent/CR7869A/es unknown
- 2005-06-10 CO CO05056566A patent/CO5700781A2/es not_active Application Discontinuation
- 2005-06-10 MA MA28324A patent/MA27605A1/fr unknown
2006
- 2006-06-06 JP JP2006157609A patent/JP3920908B2/ja not_active Expired - Fee Related
- 2006-12-27 JP JP2006352505A patent/JP4624341B2/ja not_active Expired - Fee Related
2010
- 2010-04-26 CY CY20101100367T patent/CY1110130T1/el unknown

Also Published As

Publication number	Publication date
DE60331769D1 (de)	2010-04-29
MY144338A (en)	2011-08-29
PE20040906A1 (es)	2005-01-24
NZ540505A (en)	2007-02-23
MA27605A1 (fr)	2005-11-01
JP2006232857A (ja)	2006-09-07
AU2003302878B2 (en)	2009-04-23
ATE460938T1 (de)	2010-04-15
ES2339767T3 (es)	2010-05-25
WO2004052372A1 (en)	2004-06-24
AU2003302878A1 (en)	2004-06-30
JP4624341B2 (ja)	2011-02-02
UY28117A1 (es)	2004-07-30
NO20052557L (no)	2005-09-06
PT1572214E (pt)	2010-05-06
EP1572214A1 (en)	2005-09-14
HRP20050523A2 (en)	2005-08-31
CA2508262C (en)	2009-12-01
PL377480A1 (pl)	2006-02-06
KR20050094813A (ko)	2005-09-28
MXPA05006151A (es)	2005-08-26
GEP20074272B (en)	2007-12-25
CA2508262A1 (en)	2004-06-24
PA8591601A1 (es)	2004-12-16
NL1024983A1 (nl)	2004-06-11
HN2003000401A (es)	2004-11-23
JP2007084575A (ja)	2007-04-05
AP2005003325A0 (en)	2005-06-30
AR042339A1 (es)	2005-06-15
SI1572214T1 (sl)	2010-07-30
KR100796102B1 (ko)	2008-01-21
RS51442B (sr)	2011-04-30
EA009589B1 (ru)	2008-02-28
TW200423944A (en)	2004-11-16
CR7869A (es)	2005-07-08
EA200500801A1 (ru)	2005-12-29
IS7843A (is)	2005-05-12
JP3889775B2 (ja)	2007-03-07
JP2006511599A (ja)	2006-04-06
NL1024983C2 (nl)	2005-02-01
CO5700781A2 (es)	2006-11-30
NO20052557D0 (no)	2005-05-26
CY1110130T1 (el)	2015-01-14
DK1572214T3 (da)	2010-06-07
HK1081850A1 (zh)	2006-05-26
EP1572214B1 (en)	2010-03-17
RS20050445A (sr)	2007-04-10
JP3920908B2 (ja)	2007-05-30
ECSP055850A (es)	2005-09-20
OA13014A (en)	2006-11-10

Publication	Publication Date	Title
US20090318451A1 (en)	2009-12-24	Morpholine dopamine agonists for the treatment of pain
CN107530354A (zh)	2018-01-02	使用syk抑制剂对慢性移植物抗宿主病的治疗
NO330143B1 (no)	2011-02-21	Morfolinderivater, preparat inneholdende slike, slike forbindelser for anvendelse som medikament samt anvendelse av slike for fremstilling av medikament for behandling av sykdom
US7902188B2 (en)	2011-03-08	Morpholine dopamine agonists
US20050267096A1 (en)	2005-12-01	New indazole and indolone derivatives and their use pharmaceuticals
US20050288270A1 (en)	2005-12-29	New aminopyridine derivatives and their use as pharmaceuticals
CN100488510C (zh)	2009-05-20	在性功能障碍治疗中用作多巴胺激动剂的吗啉衍生物
HK1116162A (en)	2008-12-19	Morpholine derivatives for use as dopamine agonists in the treatment of i.a. sexual dysfunction
HK1081850B (en)	2009-10-30	Morpholine derivatives for use as dopamine agonists in the treatment of i.a. sexual dysfunction
MXPA06013759A (es)	2007-02-08	Derivados de indazol e indolona y su uso como productos farmaceuticos.
UA79024C2 (en)	2007-05-10	Morpholine derivatives as dopamine agonists for treating sexual dysfunction

Legal Events

Date	Code	Title	Description
2012-07-23	MM1K	Lapsed by not paying the annual fees