Caleb. This was not Caleb the son of Jephunneh, but Caleb the son of Hezron, and therefore called the brother of Jerahmeel: See the parallel texts:

1 Chronicles 2:9 The sons also of Hezron, that were born to him; Jerahmeel, and Ram, and Chelubai.

Chelubai.

1 Chronicles 2:18,19,24 And Caleb the son of Hezron begat children of Azubah his wife, and of Jerioth: her sons are these; Jesher, and Shobab, and Ardon...

his first-born.

Genesis 49:3 Reuben, you are my firstborn, my might, and the beginning of my strength, the excellency of dignity, and the excellency of power:

Exodus 4:22,23 And you shall say to Pharaoh, Thus said the LORD, Israel is my son, even my firstborn...

Romans 8:29 For whom he did foreknow, he also did predestinate to be conformed to the image of his Son...

Hebrews 12:23 To the general assembly and church of the firstborn, which are written in heaven, and to God the Judge of all...

the father. i.e, the founder, or, as the Targum renders, 'the prince of the Ziphites;' for it was usual to call both the founder and the prince of a city its father.

Ziph.

Joshua 15:24 Ziph, and Telem, and Bealoth,

1 Samuel 23:19 Then came up the Ziphites to Saul to Gibeah, saying, Does not David hide himself with us in strong holds in the wood...

1 Samuel 26:1 And the Ziphites came to Saul to Gibeah, saying, Does not David hide himself in the hill of Hachilah, which is before Jeshimon?

the father of Hebron.

1 Chronicles 2:23,24,45,49,52 And he took Geshur, and Aram, with the towns of Jair, from them, with Kenath, and the towns thereof, even three score cities...

1 Chronicles 8:29 And at Gibeon dwelled the father of Gibeon; whose wife's name was Maachah:

Ezra 2:21-35 The children of Bethlehem, an hundred twenty and three...

Nehemiah 7:25-38 The children of Gibeon, ninety and five...