IL44636A - History N - Converted Alkanesulfonamido - Alkanesulfonamido - Al Cananoic Acids and 3 - Oxa - Alcanoic, Preparation and Raw Preparations - Google Patents

History N - Converted Alkanesulfonamido - Alkanesulfonamido - Al Cananoic Acids and 3 - Oxa - Alcanoic, Preparation and Raw Preparations

Info

Publication number: IL44636A
Authority: IL; Israel
Prior art keywords: compound; ethylene; methyl; ethyl; hydrogen
Prior art date: 1973-04-25

Application number

IL44636A

Other languages

English (en)

Hebrew (he)

Other versions

IL44636A0 (en

Original Assignee

Merck & Co Inc

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.)

1973-04-25

Filing date

1974-04-15

Publication date

1977-06-30

1974-04-15 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1974-06-30 Publication of IL44636A0 publication Critical patent/IL44636A0/xx

1977-06-30 Publication of IL44636A publication Critical patent/IL44636A/en

Links

239000002253 acid Substances 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title description 94
239000008194 pharmaceutical composition Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 118
-1 ethylene, trimethylene Chemical group 0.000 claims description 79
239000000047 product Substances 0.000 claims description 53
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
239000000203 mixture Substances 0.000 claims description 49
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
238000000034 method Methods 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 30
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 27
239000005977 Ethylene Substances 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
230000008569 process Effects 0.000 claims description 14
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 12
125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 10
239000012312 sodium hydride Substances 0.000 claims description 10
229910000104 sodium hydride Inorganic materials 0.000 claims description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 9
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000829 suppository Substances 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
AFINMNJSRUBEDE-UHFFFAOYSA-N 2-[4-[4-hydroxynonyl(methylsulfonyl)amino]butoxy]acetic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCOCC(O)=O AFINMNJSRUBEDE-UHFFFAOYSA-N 0.000 claims description 3
SUUJUAHYICGTDC-UHFFFAOYSA-N 7-[(4-hydroxy-5,5-dimethylnonyl)-methylsulfonylamino]heptanoic acid Chemical compound CCCCC(C)(C)C(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O SUUJUAHYICGTDC-UHFFFAOYSA-N 0.000 claims description 3
OLMMRXFDMOPYNV-UHFFFAOYSA-N 7-[(4-hydroxy-8,8-dimethylnonyl)-methylsulfonylamino]heptanoic acid Chemical compound CC(C)(C)CCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O OLMMRXFDMOPYNV-UHFFFAOYSA-N 0.000 claims description 3
OGPUYHYOSPKRCG-UHFFFAOYSA-N 7-[4-hydroxyundecyl(methylsulfonyl)amino]heptanoic acid Chemical compound CCCCCCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O OGPUYHYOSPKRCG-UHFFFAOYSA-N 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
AOQPTHLHEHGFFI-UHFFFAOYSA-N 7-[(4-hydroxy-4-propylheptyl)-methylsulfonylamino]heptanoic acid Chemical compound CCCC(O)(CCC)CCCN(S(C)(=O)=O)CCCCCCC(O)=O AOQPTHLHEHGFFI-UHFFFAOYSA-N 0.000 claims description 2
CKOCWHYCKMNRNF-UHFFFAOYSA-N 7-[methylsulfonyl-(9,9,9-trifluoro-4-hydroxynonyl)amino]heptanoic acid Chemical compound OC(=O)CCCCCCN(S(=O)(=O)C)CCCC(O)CCCCC(F)(F)F CKOCWHYCKMNRNF-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
230000000903 blocking effect Effects 0.000 claims 2
150000002367 halogens Chemical group 0.000 claims 2
239000013067 intermediate product Substances 0.000 claims 2
238000007911 parenteral administration Methods 0.000 claims 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 130
239000000243 solution Substances 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
239000003921 oil Substances 0.000 description 37
235000019198 oils Nutrition 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 31
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
230000015572 biosynthetic process Effects 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
238000003786 synthesis reaction Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
229910052938 sodium sulfate Inorganic materials 0.000 description 24
235000011152 sodium sulphate Nutrition 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
239000003153 chemical reaction reagent Substances 0.000 description 19
235000011167 hydrochloric acid Nutrition 0.000 description 19
229960000443 hydrochloric acid Drugs 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
150000003180 prostaglandins Chemical class 0.000 description 16
239000002904 solvent Substances 0.000 description 16
235000002639 sodium chloride Nutrition 0.000 description 15
238000003756 stirring Methods 0.000 description 15
229940094443 oxytocics prostaglandins Drugs 0.000 description 14
239000000725 suspension Substances 0.000 description 14
150000002148 esters Chemical group 0.000 description 12
239000010410 layer Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000012230 colorless oil Substances 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
ATKBLWQNGBIURV-UHFFFAOYSA-N 1-chlorononan-4-yl acetate Chemical compound CCCCCC(OC(C)=O)CCCCl ATKBLWQNGBIURV-UHFFFAOYSA-N 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
LSDSWODYQPBKJL-UHFFFAOYSA-N ethyl 7-(methanesulfonamido)heptanoate Chemical compound CCOC(=O)CCCCCCNS(C)(=O)=O LSDSWODYQPBKJL-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
230000004071 biological effect Effects 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
238000004821 distillation Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
235000001055 magnesium Nutrition 0.000 description 6
229940091250 magnesium supplement Drugs 0.000 description 6
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical group 0.000 description 6
229960002668 sodium chloride Drugs 0.000 description 6
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
GZLABWSOPXGYSC-UHFFFAOYSA-N ethyl 7-bromo-2-methylheptanoate Chemical compound CCOC(=O)C(C)CCCCCBr GZLABWSOPXGYSC-UHFFFAOYSA-N 0.000 description 5
150000004795 grignard reagents Chemical class 0.000 description 5
239000005457 ice water Substances 0.000 description 5
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 4
AZJVIHQWXFKTDB-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]heptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O AZJVIHQWXFKTDB-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
239000007818 Grignard reagent Substances 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
229930040373 Paraformaldehyde Natural products 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 4
WVMMFYVUKHYNRN-UHFFFAOYSA-N 4-(oxan-2-yloxy)nonan-1-amine Chemical compound CCCCCC(CCCN)OC1CCCCO1 WVMMFYVUKHYNRN-UHFFFAOYSA-N 0.000 description 3
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 3
QJCFJYQNICBNJE-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]-2-methylheptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCCC(C)C(O)=O QJCFJYQNICBNJE-UHFFFAOYSA-N 0.000 description 3
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
ANQJZJPZYFITRR-UHFFFAOYSA-N [1-(3-bromoprop-1-ynyl)cyclohexyl] acetate Chemical compound BrCC#CC1(OC(=O)C)CCCCC1 ANQJZJPZYFITRR-UHFFFAOYSA-N 0.000 description 3
239000003929 acidic solution Substances 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
CZKXUZDDDFAGSR-UHFFFAOYSA-N ethyl 7-[4-acetyloxynonyl(methylsulfonyl)amino]heptanoate Chemical compound CCCCCC(OC(C)=O)CCCN(S(C)(=O)=O)CCCCCCC(=O)OCC CZKXUZDDDFAGSR-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000002466 imines Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
VEAHFAXXVWTYII-UHFFFAOYSA-N methyl 7-bromo-2-methylheptanoate Chemical compound COC(=O)C(C)CCCCCBr VEAHFAXXVWTYII-UHFFFAOYSA-N 0.000 description 3
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
229960002216 methylparaben Drugs 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
IKEZOEYIWYOVCD-UHFFFAOYSA-N oct-1-yn-3-yl acetate Chemical compound CCCCCC(C#C)OC(C)=O IKEZOEYIWYOVCD-UHFFFAOYSA-N 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000002265 prevention Effects 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
229960003415 propylparaben Drugs 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
YASSLXHVJQGNOK-UHFFFAOYSA-N (1-ethynylcyclohexyl) acetate Chemical compound CC(=O)OC1(C#C)CCCCC1 YASSLXHVJQGNOK-UHFFFAOYSA-N 0.000 description 2
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OVRCZLVAFQSPHS-UHFFFAOYSA-N 2-[4-(oxan-2-yloxy)nonyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(CCCCC)OC1CCCCO1 OVRCZLVAFQSPHS-UHFFFAOYSA-N 0.000 description 2
MPSXGPCFLAGJOM-UHFFFAOYSA-M 2-tert-butyl-5-methyl-1,2-oxazol-2-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC1=CC=[N+](C(C)(C)C)O1 MPSXGPCFLAGJOM-UHFFFAOYSA-M 0.000 description 2
NCCIZKIVILDOTK-UHFFFAOYSA-N 4-ethynylheptan-4-yl acetate Chemical compound CCCC(CCC)(OC(C)=O)C#C NCCIZKIVILDOTK-UHFFFAOYSA-N 0.000 description 2
ZCYVIAZIVJNAMO-UHFFFAOYSA-N 5-chloropentyl acetate Chemical compound CC(=O)OCCCCCCl ZCYVIAZIVJNAMO-UHFFFAOYSA-N 0.000 description 2
GQPRPSPJVDGXGM-UHFFFAOYSA-N 7-[(4-hydroxy-8-methylnonyl)-methylsulfonylamino]heptanoic acid Chemical compound CC(C)CCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O GQPRPSPJVDGXGM-UHFFFAOYSA-N 0.000 description 2
AKNIDDLFJPPADY-UHFFFAOYSA-N 7-[4-acetyloxynonyl(methylsulfonyl)amino]heptanoic acid Chemical compound CCCCCC(OC(C)=O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O AKNIDDLFJPPADY-UHFFFAOYSA-N 0.000 description 2
ZONQOYOLASJJEI-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfinyl)amino]heptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)=O)CCCCCCC(O)=O ZONQOYOLASJJEI-UHFFFAOYSA-N 0.000 description 2
BYPKASNLCHRZTJ-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]-2,2-dimethylheptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCCC(C)(C)C(O)=O BYPKASNLCHRZTJ-UHFFFAOYSA-N 0.000 description 2
RYMJBTFXSOWSIO-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]-3-methylheptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCC(C)CC(O)=O RYMJBTFXSOWSIO-UHFFFAOYSA-N 0.000 description 2
OGWCHRYQCKEHBK-UHFFFAOYSA-N 7-[4-hydroxynonyl(propylsulfonyl)amino]heptanoic acid Chemical compound CCCCCC(O)CCCN(S(=O)(=O)CCC)CCCCCCC(O)=O OGWCHRYQCKEHBK-UHFFFAOYSA-N 0.000 description 2
AZJVIHQWXFKTDB-INIZCTEOSA-N 7-[[(4s)-4-hydroxynonyl]-methylsulfonylamino]heptanoic acid Chemical compound CCCCC[C@H](O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O AZJVIHQWXFKTDB-INIZCTEOSA-N 0.000 description 2
OADJHMDJKMJTBC-UHFFFAOYSA-N 7-bromo-2-methylheptanoic acid Chemical compound OC(=O)C(C)CCCCCBr OADJHMDJKMJTBC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000023275 Autoimmune disease Diseases 0.000 description 2
239000004255 Butylated hydroxyanisole Substances 0.000 description 2
239000004322 Butylated hydroxytoluene Substances 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
102000018997 Growth Hormone Human genes 0.000 description 2
108010051696 Growth Hormone Proteins 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
208000007536 Thrombosis Diseases 0.000 description 2
FJTOGOIKXQSTKI-LLVKDONJSA-N [(4r)-1-bromonon-2-yn-4-yl] acetate Chemical compound CCCCC[C@@H](OC(C)=O)C#CCBr FJTOGOIKXQSTKI-LLVKDONJSA-N 0.000 description 2
HRIFEGDDHFHVEJ-UHFFFAOYSA-N [1-(3-bromoprop-1-ynyl)cyclooctyl] acetate Chemical compound BrCC#CC1(OC(=O)C)CCCCCCC1 HRIFEGDDHFHVEJ-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000010171 animal model Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000008135 aqueous vehicle Substances 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
229940043253 butylated hydroxyanisole Drugs 0.000 description 2
235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
229940095259 butylated hydroxytoluene Drugs 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000969 carrier Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 2
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
235000004626 essential fatty acids Nutrition 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
AYDDHWOOPHEEMP-UHFFFAOYSA-N ethyl 2-(4-bromobutoxy)acetate Chemical compound CCOC(=O)COCCCCBr AYDDHWOOPHEEMP-UHFFFAOYSA-N 0.000 description 2
SVAMFQWQDXFNOS-UHFFFAOYSA-N ethyl 7-(ethylsulfonylamino)heptanoate Chemical compound CCOC(=O)CCCCCCNS(=O)(=O)CC SVAMFQWQDXFNOS-UHFFFAOYSA-N 0.000 description 2
OXLUGLGPRVLOQN-UHFFFAOYSA-N ethyl 7-(methanesulfinamido)heptanoate Chemical compound CCOC(=O)CCCCCCNS(C)=O OXLUGLGPRVLOQN-UHFFFAOYSA-N 0.000 description 2
QRPJARBLHDVPMN-UHFFFAOYSA-N ethyl 7-(propylsulfonylamino)heptanoate Chemical compound CCCS(=O)(=O)NCCCCCCC(=O)OCC QRPJARBLHDVPMN-UHFFFAOYSA-N 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
230000006870 function Effects 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
239000000122 growth hormone Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000007972 injectable composition Substances 0.000 description 2
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 2
239000000644 isotonic solution Substances 0.000 description 2
230000003907 kidney function Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
LBAZBJAMSYYBGA-UHFFFAOYSA-N n-[4-(oxan-2-yloxy)nonyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCCC(CCCCC)OC1CCCCO1 LBAZBJAMSYYBGA-UHFFFAOYSA-N 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000926 separation method Methods 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 1
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
GRYOPGAIMJFBOR-UHFFFAOYSA-N (1-chloro-4-methylnonan-4-yl) acetate Chemical compound CCCCCC(C)(OC(C)=O)CCCCl GRYOPGAIMJFBOR-UHFFFAOYSA-N 0.000 description 1
NEEAPCIRMDADSI-UHFFFAOYSA-N (1-chloro-5,5-dimethylnonan-4-yl) acetate Chemical compound CCCCC(C)(C)C(OC(C)=O)CCCCl NEEAPCIRMDADSI-UHFFFAOYSA-N 0.000 description 1
LGPQFGXCDBZAQL-UHFFFAOYSA-N (1-chloro-8-methylnonan-4-yl) acetate Chemical compound CC(C)CCCC(OC(C)=O)CCCCl LGPQFGXCDBZAQL-UHFFFAOYSA-N 0.000 description 1
BIZJXKPQMYKGSW-UHFFFAOYSA-N (1-chloro-9,9,9-trifluorononan-4-yl) acetate Chemical compound ClCCCC(OC(=O)C)CCCCC(F)(F)F BIZJXKPQMYKGSW-UHFFFAOYSA-N 0.000 description 1
DVGVUEKIOAHHSC-UHFFFAOYSA-N (1z)-1-diazodecane Chemical compound CCCCCCCCCC=[N+]=[N-] DVGVUEKIOAHHSC-UHFFFAOYSA-N 0.000 description 1
SBHCLVQMTBWHCD-METXMMQOSA-N (2e,4e,6e,8e,10e)-icosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C(O)=O SBHCLVQMTBWHCD-METXMMQOSA-N 0.000 description 1
LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 description 1
VUGRNZHKYVHZSN-QMMMGPOBSA-N (3r)-oct-1-yn-3-ol Chemical group CCCCC[C@@H](O)C#C VUGRNZHKYVHZSN-QMMMGPOBSA-N 0.000 description 1
VUGRNZHKYVHZSN-MRVPVSSYSA-N (3s)-oct-1-yn-3-ol Chemical group CCCCC[C@H](O)C#C VUGRNZHKYVHZSN-MRVPVSSYSA-N 0.000 description 1
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 1
KSDMISMEMOGBFU-UHFFFAOYSA-N (all-Z)-7,10,13-Eicosatrienoic acid Natural products CCCCCCC=CCC=CCC=CCCCCCC(O)=O KSDMISMEMOGBFU-UHFFFAOYSA-N 0.000 description 1
ZIWXVGHUDKNNSH-QPJJXVBHSA-N (e)-non-2-en-4-ol Chemical compound CCCCCC(O)\C=C\C ZIWXVGHUDKNNSH-QPJJXVBHSA-N 0.000 description 1
LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
LRGSEZPULBLFOA-UHFFFAOYSA-N 1-bromonon-2-en-4-yl acetate Chemical compound CCCCCC(OC(C)=O)C=CCBr LRGSEZPULBLFOA-UHFFFAOYSA-N 0.000 description 1
ZUASXJAXPZJPAG-UHFFFAOYSA-N 1-chloronon-8-en-4-yl acetate Chemical compound ClCCCC(OC(=O)C)CCCC=C ZUASXJAXPZJPAG-UHFFFAOYSA-N 0.000 description 1
OALZIEQUXNGQMI-UHFFFAOYSA-N 1-chlorononan-4-ol Chemical compound CCCCCC(O)CCCCl OALZIEQUXNGQMI-UHFFFAOYSA-N 0.000 description 1
ZCTKTQUONMEFHR-UHFFFAOYSA-N 1-chlorononan-4-one Chemical compound CCCCCC(=O)CCCCl ZCTKTQUONMEFHR-UHFFFAOYSA-N 0.000 description 1
GAXVGQMGJDZUMM-UHFFFAOYSA-N 1-chloroundecan-4-yl acetate Chemical compound CCCCCCCC(OC(C)=O)CCCCl GAXVGQMGJDZUMM-UHFFFAOYSA-N 0.000 description 1
QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
DHAPUKCAOFQTIT-UHFFFAOYSA-N 1-ethynylcyclooctan-1-ol Chemical compound C#CC1(O)CCCCCCC1 DHAPUKCAOFQTIT-UHFFFAOYSA-N 0.000 description 1
LYUPJHVGLFETDG-UHFFFAOYSA-N 1-phenylbutan-2-ol Chemical compound CCC(O)CC1=CC=CC=C1 LYUPJHVGLFETDG-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
JKNMJFPUESPVRV-UHFFFAOYSA-N 2-(4-bromobutoxy)acetic acid Chemical compound OC(=O)COCCCCBr JKNMJFPUESPVRV-UHFFFAOYSA-N 0.000 description 1
KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
IXUOEGRSQCCEHB-SECBINFHSA-N 4-Nonanol Natural products CCCCC[C@H](O)CCC IXUOEGRSQCCEHB-SECBINFHSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
ZNQZLTRQTHLERB-UHFFFAOYSA-N 4-ethynylheptan-4-ol Chemical compound CCCC(O)(C#C)CCC ZNQZLTRQTHLERB-UHFFFAOYSA-N 0.000 description 1
DCBJCKDOZLTTDW-UHFFFAOYSA-N 5-chloropentan-1-ol Chemical compound OCCCCCCl DCBJCKDOZLTTDW-UHFFFAOYSA-N 0.000 description 1
XLBGJFOZNOLBRU-UHFFFAOYSA-N 7-[(4-hydroxy-4-methylnonyl)-methylsulfonylamino]heptanoic acid Chemical compound CCCCCC(C)(O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O XLBGJFOZNOLBRU-UHFFFAOYSA-N 0.000 description 1
STHIFFKWNDWFSJ-UHFFFAOYSA-N 7-[(4-hydroxy-4-propylhept-2-ynyl)-methylsulfonylamino]heptanoic acid Chemical compound CCCC(O)(CCC)C#CCN(S(C)(=O)=O)CCCCCCC(O)=O STHIFFKWNDWFSJ-UHFFFAOYSA-N 0.000 description 1
BVZCICPBNIINFR-UHFFFAOYSA-N 7-[4-hydroxynon-2-ynyl(methylsulfonyl)amino]heptanoic acid Chemical compound CCCCCC(O)C#CCN(S(C)(=O)=O)CCCCCCC(O)=O BVZCICPBNIINFR-UHFFFAOYSA-N 0.000 description 1
BTZANFUAMDZSKB-UHFFFAOYSA-N 7-[4-hydroxynon-8-enyl(methylsulfonyl)amino]heptanoic acid Chemical compound OC(=O)CCCCCCN(S(=O)(=O)C)CCCC(O)CCCC=C BTZANFUAMDZSKB-UHFFFAOYSA-N 0.000 description 1
PDRDCCIBASPWOO-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]-3,3-dimethylheptanoic acid Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCC(C)(C)CC(O)=O PDRDCCIBASPWOO-UHFFFAOYSA-N 0.000 description 1
SQABNILCWYMNJZ-UHFFFAOYSA-N 7-[4-hydroxynonyl(methylsulfonyl)amino]heptanamide Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(N)=O SQABNILCWYMNJZ-UHFFFAOYSA-N 0.000 description 1
AZJVIHQWXFKTDB-MRXNPFEDSA-N 7-[[(4r)-4-hydroxynonyl]-methylsulfonylamino]heptanoic acid Chemical compound CCCCC[C@@H](O)CCCN(S(C)(=O)=O)CCCCCCC(O)=O AZJVIHQWXFKTDB-MRXNPFEDSA-N 0.000 description 1
JCSLLZNGINBBCQ-ZRDIBKRKSA-N 7-[[(e)-4-hydroxynon-2-enyl]-methylsulfonylamino]heptanoic acid Chemical compound CCCCCC(O)\C=C\CN(S(C)(=O)=O)CCCCCCC(O)=O JCSLLZNGINBBCQ-ZRDIBKRKSA-N 0.000 description 1
JHFBNEUIYAVJPR-UHFFFAOYSA-N 7-[ethylsulfonyl(4-hydroxynonyl)amino]heptanoic acid Chemical compound CCCCCC(O)CCCN(S(=O)(=O)CC)CCCCCCC(O)=O JHFBNEUIYAVJPR-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
208000031295 Animal disease Diseases 0.000 description 1
244000186140 Asperula odorata Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
NBKFZZPFKFZVOP-FYWRMAATSA-N CCCCCC(OC(C)=O)\C=C\CN(S(C)(=O)=O)CCCCCCC(=O)OCC Chemical compound CCCCCC(OC(C)=O)\C=C\CN(S(C)(=O)=O)CCCCCCC(=O)OCC NBKFZZPFKFZVOP-FYWRMAATSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
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 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
206010013883 Dwarfism Diseases 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
235000008526 Galium odoratum Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
108010024636 Glutathione Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
101000606728 Homo sapiens Pepsin A-3 Proteins 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
102100039657 Pepsin A-3 Human genes 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
208000006399 Premature Obstetric Labor Diseases 0.000 description 1
206010036600 Premature labour Diseases 0.000 description 1
IXUOEGRSQCCEHB-UHFFFAOYSA-N Propyl-n-amyl-carbinol Natural products CCCCCC(O)CCC IXUOEGRSQCCEHB-UHFFFAOYSA-N 0.000 description 1
TYBCSQFBSWACAA-UHFFFAOYSA-N Propyl-pentyl-keton Natural products CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 description 1
MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 description 1
241000534944 Thia Species 0.000 description 1
HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
NCRVLUJNKJFEKS-UHFFFAOYSA-N [1-[3-(diethylamino)prop-1-ynyl]cyclohexyl] acetate Chemical compound CCN(CC)CC#CC1(OC(C)=O)CCCCC1 NCRVLUJNKJFEKS-UHFFFAOYSA-N 0.000 description 1
APEDQZZHGRBZIK-UHFFFAOYSA-N [1-[3-(diethylamino)prop-1-ynyl]cyclooctyl] acetate Chemical compound CCN(CC)CC#CC1(OC(C)=O)CCCCCCC1 APEDQZZHGRBZIK-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000012387 aerosolization Methods 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000000746 allylic group Chemical group 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
150000001450 anions Chemical class 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
230000003243 anti-lipolytic effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
239000003793 antidiarrheal agent Substances 0.000 description 1
229940125714 antidiarrheal agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
YZXBAPSDXZZRGB-CGRWFSSPSA-N arachidonic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCC(O)=O YZXBAPSDXZZRGB-CGRWFSSPSA-N 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-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
230000003851 biochemical process Effects 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000001851 biosynthetic effect Effects 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
229940095074 cyclic amp Drugs 0.000 description 1
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
239000004914 cyclooctane Substances 0.000 description 1
150000001940 cyclopentanes Chemical class 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
MLXQOFPEBIXBNI-UHFFFAOYSA-N diethyl 2-(5-acetyloxypentyl)-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)CCCCCOC(C)=O MLXQOFPEBIXBNI-UHFFFAOYSA-N 0.000 description 1
UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
ZZTSQZQUWBFTAT-UHFFFAOYSA-N diethylcyanamide Chemical compound CCN(CC)C#N ZZTSQZQUWBFTAT-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000012971 dimethylpiperazine Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
FHXBMXJMKMWVRG-SLHNCBLASA-N estradiol acetate Chemical compound C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2CCC3=CC(OC(=O)C)=CC=C3[C@H]21 FHXBMXJMKMWVRG-SLHNCBLASA-N 0.000 description 1
RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
GKVKEWIQHDKQPC-UHFFFAOYSA-N ethyl 7-[(4-acetyloxy-4-methylnonyl)-methylsulfonylamino]heptanoate Chemical compound CCCCCC(C)(OC(C)=O)CCCN(S(C)(=O)=O)CCCCCCC(=O)OCC GKVKEWIQHDKQPC-UHFFFAOYSA-N 0.000 description 1
QADVRBBNJWGOGI-UHFFFAOYSA-N ethyl 7-[(4-acetyloxy-4-propylhept-2-ynyl)-methylsulfonylamino]heptanoate Chemical compound CCCC(CCC)(OC(C)=O)C#CCN(S(C)(=O)=O)CCCCCCC(=O)OCC QADVRBBNJWGOGI-UHFFFAOYSA-N 0.000 description 1
WIIBYGZQQIZXDZ-UHFFFAOYSA-N ethyl 7-[(4-acetyloxy-5,5-dimethylnonyl)-methylsulfonylamino]heptanoate Chemical compound CCCCC(C)(C)C(OC(C)=O)CCCN(S(C)(=O)=O)CCCCCCC(=O)OCC WIIBYGZQQIZXDZ-UHFFFAOYSA-N 0.000 description 1
PUPBALCFJKMYMH-UHFFFAOYSA-N ethyl 7-[(4-acetyloxy-8,8-dimethylnonyl)-methylsulfonylamino]heptanoate Chemical compound CCOC(=O)CCCCCCN(S(C)(=O)=O)CCCC(OC(C)=O)CCCC(C)(C)C PUPBALCFJKMYMH-UHFFFAOYSA-N 0.000 description 1
IEIULHHLRUBADT-UHFFFAOYSA-N ethyl 7-[4-acetyloxynon-8-enyl(methylsulfonyl)amino]heptanoate Chemical compound CCOC(=O)CCCCCCN(S(C)(=O)=O)CCCC(OC(C)=O)CCCC=C IEIULHHLRUBADT-UHFFFAOYSA-N 0.000 description 1
IFOSDCYJKVMANF-UHFFFAOYSA-N ethyl 7-[4-acetyloxynonyl(ethylsulfonyl)amino]heptanoate Chemical compound CCCCCC(OC(C)=O)CCCN(S(=O)(=O)CC)CCCCCCC(=O)OCC IFOSDCYJKVMANF-UHFFFAOYSA-N 0.000 description 1
WENHCXUENJNJDZ-UHFFFAOYSA-N ethyl 7-[4-acetyloxynonyl(methylsulfinyl)amino]heptanoate Chemical compound CCCCCC(OC(C)=O)CCCN(S(C)=O)CCCCCCC(=O)OCC WENHCXUENJNJDZ-UHFFFAOYSA-N 0.000 description 1
GEHPPIBGTKBJAU-UHFFFAOYSA-N ethyl 7-[4-acetyloxynonyl(propylsulfonyl)amino]heptanoate Chemical compound CCCCCC(OC(C)=O)CCCN(S(=O)(=O)CCC)CCCCCCC(=O)OCC GEHPPIBGTKBJAU-UHFFFAOYSA-N 0.000 description 1
ZUIGISFMVIERIX-UHFFFAOYSA-N ethyl 7-[4-acetyloxyundecyl(methylsulfonyl)amino]heptanoate Chemical compound CCCCCCCC(OC(C)=O)CCCN(S(C)(=O)=O)CCCCCCC(=O)OCC ZUIGISFMVIERIX-UHFFFAOYSA-N 0.000 description 1
OOBFNDGMAGSNKA-UHFFFAOYSA-N ethyl 7-bromoheptanoate Chemical compound CCOC(=O)CCCCCCBr OOBFNDGMAGSNKA-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000035558 fertility Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
208000022059 functional hyperemia Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229960003180 glutathione Drugs 0.000 description 1
235000003969 glutathione Nutrition 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000037356 lipid metabolism Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000005374 membrane filtration Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
USRPHJBSMMPNLJ-UHFFFAOYSA-N methyl 7-[4-hydroxynonyl(methylsulfonyl)amino]heptanoate Chemical compound CCCCCC(O)CCCN(S(C)(=O)=O)CCCCCCC(=O)OC USRPHJBSMMPNLJ-UHFFFAOYSA-N 0.000 description 1
YIJIVYXDADQOIA-UHFFFAOYSA-N methyl 7-iodo-2,2-dimethylheptanoate Chemical compound COC(=O)C(C)(C)CCCCCI YIJIVYXDADQOIA-UHFFFAOYSA-N 0.000 description 1
USCCPHJJQIICKJ-UHFFFAOYSA-N methyl 7-iodo-3,3-dimethylheptanoate Chemical compound COC(=O)CC(C)(C)CCCCI USCCPHJJQIICKJ-UHFFFAOYSA-N 0.000 description 1
HOLXLNLZLRQLRP-UHFFFAOYSA-N methyl 7-iodo-3-methylheptanoate Chemical compound COC(=O)CC(C)CCCCI HOLXLNLZLRQLRP-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
BOZILQFLQYBIIY-INTXDZFKSA-N mevinic acid Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)CCC=C21 BOZILQFLQYBIIY-INTXDZFKSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
ZWRUINPWMLAQRD-UHFFFAOYSA-N n-Nonyl alcohol Natural products CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
WMFDOJLPEUKEHZ-UHFFFAOYSA-N non-2-en-4-yl acetate Chemical compound CCCCCC(OC(C)=O)C=CC WMFDOJLPEUKEHZ-UHFFFAOYSA-N 0.000 description 1
125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
125000006353 oxyethylene group Chemical group 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001993 poloxamer 188 Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
208000026440 premature labor Diseases 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 1
KSIRMUMXJFWKAC-FHJHOUOTSA-N prostaglandin A3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O KSIRMUMXJFWKAC-FHJHOUOTSA-N 0.000 description 1
239000002089 prostaglandin antagonist Substances 0.000 description 1
230000002997 prostaglandinlike Effects 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229940124550 renal vasodilator Drugs 0.000 description 1
210000004994 reproductive system Anatomy 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
238000012552 review Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000000080 wetting agent Substances 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
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Hematology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyrane Compounds (AREA)

IL44636A 1973-04-25 1974-04-15 History N - Converted Alkanesulfonamido - Alkanesulfonamido - Al Cananoic Acids and 3 - Oxa - Alcanoic, Preparation and Raw Preparations IL44636A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US35427373A	1973-04-25	1973-04-25
US41834173A	1973-11-23	1973-11-23

Publications (2)

Publication Number	Publication Date
IL44636A0 IL44636A0 (en)	1974-06-30
IL44636A true IL44636A (en)	1977-06-30

Family

ID=26998324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44636A IL44636A (en)	1973-04-25	1974-04-15	History N - Converted Alkanesulfonamido - Alkanesulfonamido - Al Cananoic Acids and 3 - Oxa - Alcanoic, Preparation and Raw Preparations

Country Status (14)

Country	Link
JP (1)	JPS5013331A (fr)
AR (1)	AR211319A1 (fr)
BE (1)	BE814089A (fr)
CA (1)	CA1044701A (fr)
CH (1)	CH605714A5 (fr)
DE (1)	DE2419860A1 (fr)
ES (1)	ES425591A1 (fr)
FR (1)	FR2226995B1 (fr)
GB (1)	GB1429092A (fr)
IE (1)	IE39227B1 (fr)
IL (1)	IL44636A (fr)
NL (1)	NL7404839A (fr)
NO (1)	NO139438C (fr)
SE (1)	SE410185B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3991087A (en)	1973-12-13	1976-11-09	Merck & Co., Inc.	8-Halo-11,12-secoprostaglandins
AT351182B (de) *	1974-06-25	1979-07-10	Merck & Co Inc	Verfahren zur herstellung von neuen 9-thia-, 9-oxothia- und 9-dioxothia- 11,12-secoprosta- glandinen
US4018802A (en) *	1975-04-09	1977-04-19	Merck & Co., Inc.	9-Thia- and oxothia- and 9-dioxothia-11,12-seco-prostaglandins and processes
US4128564A (en) *	1976-03-22	1978-12-05	Merck & Co., Inc.	9-Thia- and oxothia- and 9-dioxothia-11,12-seco-prostaglandins
US4112236A (en)	1977-04-04	1978-09-05	Merck & Co., Inc.	Interphenylene 8-aza-9-dioxothia-11,12-secoprostaglandins

1974
- 1974-04-08 SE SE7404695A patent/SE410185B/xx unknown
- 1974-04-09 NL NL7404839A patent/NL7404839A/xx not_active Application Discontinuation
- 1974-04-09 NO NO74741309A patent/NO139438C/no unknown
- 1974-04-15 IL IL44636A patent/IL44636A/en unknown
- 1974-04-16 FR FR7413154A patent/FR2226995B1/fr not_active Expired
- 1974-04-19 IE IE843/74A patent/IE39227B1/xx unknown
- 1974-04-22 GB GB1752274A patent/GB1429092A/en not_active Expired
- 1974-04-22 AR AR253388A patent/AR211319A1/es active
- 1974-04-23 ES ES425591A patent/ES425591A1/es not_active Expired
- 1974-04-24 CA CA198,456A patent/CA1044701A/fr not_active Expired
- 1974-04-24 DE DE2419860A patent/DE2419860A1/de active Pending
- 1974-04-24 CH CH563474A patent/CH605714A5/xx not_active IP Right Cessation
- 1974-04-24 BE BE143523A patent/BE814089A/fr unknown
- 1974-04-25 JP JP49046074A patent/JPS5013331A/ja active Pending

Also Published As

Publication number	Publication date
AU6797374A (en)	1975-10-23
ES425591A1 (es)	1976-11-01
SE410185B (sv)	1979-10-01
AR211319A1 (es)	1977-11-20
JPS5013331A (fr)	1975-02-12
FR2226995A1 (fr)	1974-11-22
IE39227B1 (en)	1978-08-30
IL44636A0 (en)	1974-06-30
GB1429092A (en)	1976-03-24
CH605714A5 (fr)	1978-10-13
NO139438C (no)	1979-03-14
BE814089A (fr)	1974-10-24
NO139438B (no)	1978-12-04
CA1044701A (fr)	1978-12-19
DE2419860A1 (de)	1974-11-07
FR2226995B1 (fr)	1977-01-28
NO741309L (no)	1974-10-28
IE39227L (en)	1974-10-25
NL7404839A (fr)	1974-10-29

Publication	Publication Date	Title
US4033996A (en)	1977-07-05	8-Aza-9-oxo(and dioxo)-thia-11,12-secoprostaglandins
US3987091A (en)	1976-10-19	11,12-secoprostaglandins
US4066692A (en)	1978-01-03	11,12-secoprostaglandins
US3991106A (en)	1976-11-09	16-Ethers of 8-aza-9-dioxothia-11,12-seco-prostaglandins
US3751463A (en)	1973-08-07	Cyclopentane derivatives
US4018802A (en)	1977-04-19	9-Thia- and oxothia- and 9-dioxothia-11,12-seco-prostaglandins and processes
US4022794A (en)	1977-05-10	Novel analogs of prostaglandins with 4-oxo-thiazolidinyl nucleus and method of preparation thereof
US3991087A (en)	1976-11-09	8-Halo-11,12-secoprostaglandins
US4020177A (en)	1977-04-26	Substituted phenoxy-tridecanoic acids
US4102888A (en)	1978-07-25	3-Thiazolidinyl heptanoic acids
US3989749A (en)	1976-11-02	11,12-Secoprostaglandins
US4112236A (en)	1978-09-05	Interphenylene 8-aza-9-dioxothia-11,12-secoprostaglandins
US4091107A (en)	1978-05-23	8-Aza-9-oxo(and dioxo)-thia-11,12-secoprostaglandins
US4055596A (en)	1977-10-25	11,12-Seco-prostaglandins
US4126629A (en)	1978-11-21	Substituted phenoxy-tridecenoic acids/esters
US4092356A (en)	1978-05-30	11,12-Secoprostaglandins
US4097504A (en)	1978-06-27	11,12-Secoprostaglandins
US4260771A (en)	1981-04-07	Interphenylene 9-thia-11-oxo-12-azaprostanoic acid compounds
US4175203A (en)	1979-11-20	Interphenylene 11,12-secoprostaglandins
US4150235A (en)	1979-04-17	Interphenylene 11,12-secoprostaglandins
US4085125A (en)	1978-04-18	9-Thia-, 9-oxothia-, and 9-dioxothia-11,12-seco-prostaglandins and processes
US4128564A (en)	1978-12-05	9-Thia- and oxothia- and 9-dioxothia-11,12-seco-prostaglandins
US4055597A (en)	1977-10-25	10-Aza-11,12-secoprostaglandins
US4059602A (en)	1977-11-22	8-Methyl-, phenyl-, or substituted phenyl-11,12-secoprostaglandins
US4059601A (en)	1977-11-22	8-Halo-11,12-secoprostaglandins